Organic electroluminescence element

ABSTRACT

An organic electroluminescent device having an anode, a cathode, and a light-emitting layer between the anode and the cathode, wherein the light-emitting layer contains at least a first organic compound, a second organic compound and a third organic compound satisfying the following formula (A), the second organic compound is a delayed fluorescent material, and the third organic compound is a light-emitting material, has a high light emission efficiency. Formula (A): E S1 (A)&gt;E S1 (B)&gt;E S1 (C) wherein E S1 (A), E S1 (B) and E S1 (C) each represent a lowest excited singlet energy level of the first organic compound, the second organic compound and the third organic compound, respectively.

TECHNICAL FIELD

The present invention relates to an organic electroluminescent devicehaving a high light emission efficiency.

BACKGROUND ART

Studies for enhancing the light emission efficiency of organiclight-emitting devices such as organic electroluminescent devices(organic EL devices) are being made actively. In particular, variouskinds of efforts have been made for increasing light emission efficiencyby newly developing materials for use in a light-emitting layer.

Among them, there is known a study relating to an organicelectroluminescent device that utilizes a host material and a guestmaterial (light-emitting dopant) in such a manner that the excitationenergy generated by the host material is transferred to the guestmaterial for light emission.

PTLs 1 and 2 disclose an organic electroluminescent device using a hostmaterial, a light-emitting dopant and an assist dopant as materials forthe light-emitting layer therein. In the organic electroluminescentdevice, the assist dopant is to complement carrier transfer in thelight-emitting layer, and for example, for complement of electrontransfer, a hole transfer material such as a phenylamine derivative isused, while for complement of hole transfer, an electron transfermaterial is used. In these publications, it is described that by usingsuch an assist dopant, the probability of carrier recombinationincreases and the light emission efficiency of the organicelectroluminescent device can be thereby increased.

PTL 3 discloses an organic electroluminescent device that uses a firstdopant containing a material capable of converting a triplet excitationenergy into light emission and having a first energy gap, a seconddopant containing a material capable of converting a a tripletexcitation energy into light emission and having a second energy gaplarger than the first energy gap, and a host material having a thirdenergy gap larger than the second energy gap, as materials for thelight-emitting layer therein, in which organic metal complexes havingiridium as a center metal are described as examples of the first dopantand the second dopant. In this publication, it is described that, byusing such two kinds of dopants and a host material as combined, thelight emission efficiency of the organic electroluminescent device canbe increased and the driving voltage thereof is lowered, and inaddition, the emission life time thereof is thereby prolonged.

CITATION LIST Patent Literature

PTL 1: JP 2005-108726 A

PTL 2: JP 2005-108727 A

PTL 3: JP 2006-41395 A

SUMMARY OF INVENTION Technical Problem

However, the organic electroluminescent device of PTLs 1 and 2 could notsufficiently increase light emission efficiency owing to the followingreasons.

Specifically, in an organic electroluminescent device using a hostmaterial and a light-emitting dopant, when holes and electrons areinjected into the light-emitting layer, the holes and the electrons arerecombined mainly in the molecule of the host material to generateexcitation energy and the host material becomes in an excited singletstate and an excited triplet state. Regarding the probability of formingexcitons in an excited single state (singlet excitons) and excitons inan excited triplet state (triplet excitons), statistically, the singletexcitons are 25% and the triplet excitons are 75%.

With that, in the case where the light-emitting dopant is any ofperylene derivatives, oxadiazole derivatives and anthracene derivativesas exemplified in the patent publications, the energy of the singletexciton is transferred to the light-emitting dopant so that thelight-emitting dopant is thereby excited to be in an excited singletstate. The light-emitting dopant thus excited in an excited singletstate emits fluorescence when it is thereafter restored to a groundstate. As opposed to this, the energy of the triplet excitons is nottransferred to the light-emitting dopant, and the triplet exciton doesnot contribute toward light emission but is restored to a ground stateas it is. Consequently, in the organic electroluminescent device of thetype, even though the probability of recombination of carriers isincreased by the assist dopant, the energy of the triplet excitons thataccount for 75% of all the excitons will run to waste, and theimprovement of light efficiency in this case is therefore limited.

On the other hand, the organic electroluminescent device of PTL 3 uses amaterial capable of converting triplet excitation energy into lightemission such as an iridium organic metal complex as the first dopanttherein. An iridium organic metal complex is known to receive excitedtriplet energy from a host material owing to the effect of the heavymetal thereof, and also in this system, it is considered that the firstdopant can receive the energy of the host material in an excited tripletstate and the second dopant to convert it into light emission. However,the excited triplet state has a long lifetime therefore causing energydeactivation owing to saturation of the excited state and interactionwith the exciton in an excited triplet state, and in general, therefore,phosphorescence quantum yield is not high. Consequently, it is difficultto sufficiently increase the light emission efficiency of the organicelectroluminescent device of the patent publication that mainly utilizeslight emission (phosphorescence) from triplet excitation energy.

Given the situation and taking these technical problems in conventionalart into consideration, the present inventors have promoted assiduousstudies for the purpose of providing an organic electroluminescentdevice having a high light emission efficiency.

Solution to Problem

As a result of further assiduous studies, the present inventors havefound that, when a delayed fluorescent material is used as an assistdopant, the delayed fluorescent material in an excited triplet state canundergo reverse intersystem crossing from the excited triplet state toan excited singlet state, and therefore as a result, the tripletexcitation energy can be converted into fluorescence, and an organicelectroluminescent device having a high light emission efficiency can bethereby provided. Based on these findings, the present inventors havereached the following present invention as a means for solving theabove-mentioned problems.

[1] An organic electroluminescent device having an anode, a cathode, andat least one organic layer that contains a light-emitting layer betweenthe anode and the cathode, wherein the light-emitting layer contains atleast a first organic compound, a second organic compound and a thirdorganic compound satisfying the following formula (A), the secondorganic compound is a delayed fluorescent material, and the thirdorganic compound is a light-emitting material:

E_(S1)(A)>E_(S1)(B)>E_(S1)(C)  Formula (A)

wherein E_(S1)(A) represents a lowest excited singlet energy level ofthe first organic compound, E_(S1)(B) represents a lowest excitedsinglet energy level of the second organic compound, E_(S1)(C)represents a lowest excited singlet energy level of the third organiccompound.[2] The organic electroluminescent device according to [1], wherein thesecond organic compound is such that the energy difference ΔE_(st)between the lowest excited singlet state and the lowest excited tripletstate at 77 K thereof is 0.3 eV or less.[3] The organic electroluminescent device according to [1], wherein thesecond organic compound is such that the energy difference ΔE_(st)between the lowest excited singlet state and the lowest excited tripletstate at 77 K thereof is 0.08 eV or less.[4] The organic electroluminescent device according to any one of [1] to[3], wherein the first organic compound and the second organic compoundsatisfy the following formula (B):

E_(T1)(A)>E_(T1)(B)  Formula (B)

wherein E_(T1)(A) represents a lowest excited triplet energy level at 77K of the first organic compound, E n(B) represents a lowest excitedtriplet energy level at 77 K of the second organic compound.[5] The organic electroluminescent device according to any one of [1] to[4], wherein the third organic compound emits fluorescence whenreturning back to the ground state energy level from the lowest excitedsinglet energy level.[6] The organic electroluminescent device according to any one of [1] to[5], wherein the content of the second organic compound in thelight-emitting layer is smaller than the content of the first organiccompound therein.[7] The organic electroluminescent device according to any one of [1] to[6], wherein the light-emitting layer contains two or more compounds asthe third organic compound.[8] The organic electroluminescent device according to any one of [1] to[7], wherein the light-emitting layer contains one or more organiccompounds in addition to the first organic compound, the second organiccompound and the third organic compound.[9] The organic electroluminescent device according to any one of [1] to[8], wherein the second organic compound is a compound represented bythe following general formula (1):

(A)m-L-(D)n  General Formula (1)

wherein L represents an (m+n)-valent aromatic linking group; Arepresents a group having a positive Hammett's σ_(p) value, or a phenylgroup; D represents a group having a negative Hammett's σ_(p) value(except a phenyl group); m represents an integer of 1 or more; nrepresents an integer of 2 or more; when m is 2 or more, plural A's maybe the same as or different from each other; two of plural D's aregroups containing an aromatic ring common to them but having a differentstructure.[10] The organic electroluminescent device according to any one of [1]to [8], wherein the second organic compound is a compound represented bythe following general formula (12):

wherein at least three of R¹¹ to R¹⁵ are selected from a substituted orunsubstituted diarylamino group (provided that the two aryl groupsconstituting the diarylamino group may bond to each other) and a halogenatom, and all the selected groups are not the same, and at least one isa substituted or unsubstituted diarylamino group(provided that the twoaryl groups constituting the diarylamino group may bond to each other),and the remaining 0 to 2 each represent a hydrogen atom, a substitutedor unsubstituted aryl group, or a cyano group.[11] The organic electroluminescent device according to any one of [1]to [8], wherein the second organic compound is a compound represented bythe following general formula (14):

wherein at least three of R¹¹, R¹², R¹⁴ and R¹⁵ are selected from asubstituted or unsubstituted diarylamino group (provided that the twoaryl groups constituting the diarylamino group may bond to each other)and a halogen atom, and all the selected groups are not the same, and atleast one is a substituted or unsubstituted diarylamino group(providedthat the two aryl groups constituting the diarylamino group may bond toeach other), and the remaining 0 to 1 represents a hydrogen atom, asubstituted or unsubstituted aryl group, or a cyano group.[12] A compound represented by the following general formula (13):

wherein at least three of R¹¹ to R¹⁵ each represent a substituted orunsubstituted carbazol-9-yl group, and all these at least threesubstituted or unsubstituted carbazol-9-yl groups are not the same, andare not substituted with a substituted or unsubstituted diarylaminogroup (provided that the two aryl groups constituting the diarylaminogroup may bond to each other), the remaining 0 to 2 each represent ahydrogen atom, a substituted or unsubstituted aryl group, a halogenatom, or a cyano group.[13] A mixture at least containing a first organic compound, a secondorganic compound and a third organic compound satisfying the followingformula (A), in which the second organic compound is a delayedfluorescent material, and the third organic compound is a light-emittingmaterial:

E_(S1)(A)>E_(S1)(B)>E_(S1)(C)  Formula (A)

wherein E_(S1)(A) represents a lowest excited singlet energy level ofthe first organic compound, E_(S1)(B) represents a lowest excitedsinglet energy level of the second organic compound, E_(S1)(C)represents a lowest excited singlet energy level of the third organiccompound.[14] A film at least containing a first organic compound, a secondorganic compound and a third organic compound satisfying the followingformula (A), in which the second organic compound is a delayedfluorescent material, and the third organic compound is a light-emittingmaterial:

E_(S1)(A)>E_(S1)(B)>E_(S1)(C)  Formula (A)

wherein E_(S1)(A) represents a lowest excited singlet energy level ofthe first organic compound, E_(S1)(B) represents a lowest excitedsinglet energy level of the second organic compound, E_(S1)(C)represents a lowest excited singlet energy level of the third organiccompound.

Advantageous Effects of Invention

The organic electroluminescent device of the present invention usesthree kinds of organic compounds satisfying a specific condition ascombined, and is characterized by having an extremely high lightemission efficiency. In particular, in the present invention where thethird organic compound is a compound that emits fluorescence whenreturning back to a ground state energy level from the lowest excitedsinglet energy level, the light emission efficiency of the organicelectroluminescent device can be greatly enhanced.

BRIEF DESCRIPTION OF DRAWING

FIG. 1 This is a schematic cross-sectional view showing a layerconfiguration example of an organic electroluminescent device.

DESCRIPTION OF EMBODIMENTS

The contents of the invention will be described in detail below. Theconstitutional elements may be described below with reference torepresentative embodiments and specific examples of the invention, butthe invention is not limited to the embodiments and the examples. In thedescription herein, a numerical range expressed as “to” means a rangethat includes the numerical values described before and after “to” asthe upper limit and the lower limit. The hydrogen atom that is presentin the molecule of the compound used in the invention is notparticularly limited in isotope species, and for example, all thehydrogen atoms in the molecule may be ¹H, and all or a part of them maybe ²H (deuterium (D)).

[Layer Configuration of Organic Electroluminescent Device]

The organic electroluminescent device of the present invention is soconfigured as to have an anode, a cathode, and an organic layer formedbetween the anode and the cathode. The organic layer contains at least alight-emitting layer, and the organic electroluminescent device of thepresent invention is characterized by the configuration of thelight-emitting layer. The configuration is described in detailhereinunder.

The organic layer may be composed of a light-emitting layer alone, ormay have any other one or more organic layers than the light-emittinglayer. Such other organic layers include a hole transport layer, a holeinjection layer, an electron blocking layer, a hole blocking layer, anelectron injection layer, an electron transport layer, and an excitonblocking layer. The hole transport layer may be a hole injectiontransport layer having a hole injection function, and the electrontransport layer may be an electron injection transport layer having anelectron injection function. A specific configuration example of anorganic electroluminescent device is shown in FIG. 1. In FIG. 1, 1 is asubstrate, 2 is an anode, 3 is a hole injection layer, 4 is a holetransport layer, 5 is a light-emitting layer, 6 is an electron transportlayer, and 7 is a cathode.

In the following, the constituent members and the layers of the organicelectroluminescent device are described.

[Light-Emitting Layer]

The light-emitting layer is a layer in which holes and electronsinjected from an anode and a cathode are recombined to give excitons forlight emission.

In organic electroluminescent device of the present invention, thelight-emitting layer contains at least a first organic compound, asecond organic compound and a third organic compound satisfying thefollowing formula (A), the second organic compound is a delayedfluorescent material, and the third organic compound is a light-emittingmaterial.

E_(S1)(A)>E_(S1)(B)>E_(S1)(C)  Formula (A)

wherein E_(S1)(A) represents a lowest excited singlet energy level ofthe first organic compound, E_(S1)(B) represents a lowest excitedsinglet energy level of the second organic compound, E_(S1)(C)represents a lowest excited singlet energy level of the third organiccompound.

The “delayed fluorescent material” in the present invention is anorganic compound which, after having transited to an excited tripletstate, can undergo reverse intersystem crossing to an excited singletstate, and which can emit fluorescence when returning back to the groundstate from the excited singlet state. The lifetime of the light to occurthrough the reverse intersystem crossing from the excited triplet stateto the excited single state is longer than that of ordinary fluorescence(instantaneous fluorescence) or phosphorescence, and therefore the lightcan be observed as a fluorescence delayed from them. Consequently, suchfluorescence is referred to as “delayed fluorescence”.

In the light-emitting layer, the lowest excited singlet energyE_(S1)(A), E_(S1)(B) and E_(S1)(C) of the first organic compound to thethird organic compound satisfy the above-mentioned formula (A), and thesecond organic compound is a delayed fluorescent material, and thereforethe excitation energy to be generated by recombination of the holes andthe electrons injected into the light-emitting layer can be efficientlyconverted into fluorescence and can provide a high light emissionefficiency. This is considered to be because of the following reasons.

Specifically, in the light-emitting layer, when excitation energy isgenerated by recombination of holes and electrons, the organic compoundscontained in the light-emitting layer transit from the ground state toan excited singlet state and an excited triplet state. The probabilityof formation of the organic compound in an excited singlet state(singlet exciton) and the organic compound in an excited triplet state(triplet exciton) is statistically such that the singlet excitonaccounts for 25% and the triplet exciton accounts for 75%. With that,the energy of the first organic compound and the second organic compoundin an excited singlet state of the excitons transfers to the thirdorganic compound, and the third organic compound in a ground statetransits to an excited singlet state. The third organic compound thathas been in an excited singlet state thereafter emits fluorescence whenreturning back to the ground state.

At that time, in the organic electroluminescent device of the presentinvention, the second organic compound is a delayed fluorescentmaterial, and therefore the second organic compound in an excitedtriplet state undergoes reverse intersystem crossing to an excitedsinglet state, and the singlet excitation energy by the reverseintersystem crossing also transfers to the third organic compound.Consequently, the second organic compound in an excited triplet statehaving a large abundance ratio can indirectly contribute toward lightemission, and the light-emitting layer of the type can exponentiallyincrease the light emission efficiency of the organic electroluminescentdevice as compared with the configuration where the light-emitting layerdoes not contain a second organic compound.

In the organic electroluminescent device of the present invention,although light emission occurs mainly from the third organic compound, apart of light emission may be light emission partly from the firstorganic compound and the second organic compound. The light emissionincludes both fluorescence emission and delayed fluorescence emission.

In the organic electroluminescent device of the present invention, thetype and the combination of the first organic compound, the secondorganic compound and the third organic compound are not specificallylimited so far as the above formula (A) is satisfied, the second organiccompound is a delayed fluorescent material, and the third organiccompound is a light-emitting material. Preferably, the organicelectroluminescent device of the present invention further satisfies thefollowing formula (B) for realizing a further higher light emissionefficiency.

E_(T1)(A)>E_(T1)(B)  Formula (B)

wherein E_(T1)(A) represents a lowest excited triplet energy level at 77K of the first organic compound, E_(T1)(B) represents a lowest excitedtriplet energy level at 77 K of the second organic compound. Therelationship between the lowest excited triplet energy level E_(T1)(B)at 77 K of the second organic compound and the lowest excited tripletenergy level E_(T1)(C) at 77 K of the third organic compound is notspecifically limited, but for example, can be so selected as to satisfyE_(T1)(B)>E_(T1)(C).

In the following, the present invention will be described morespecifically with reference to preferred examples thereof, but the scopeof the present invention should not be limitatively interpreted by thedescription based on the following specific examples.

First, the first compound, the second compound and the third compoundare described in that order, and the other materials and elements aredescribed thereafter.

[First Organic Compound]

The first organic compound is an organic compound having a larger lowestexcited singlet energy than the second organic compound and the thirdorganic compound, and has a function as a host material to take a rolein carrier transport and also a function to trap the energy of the thirdorganic compound in the compound. Accordingly, the third organiccompound can efficiently convert the energy generated by recombinationof holes and electrons in the molecule and the energy having receivedfrom the first organic compound and the second organic compound intolight emission, and an organic electroluminescent device having a highlight emission efficiency can be thereby realized.

The first organic compound is preferably an organic compound having ahole transport ability and an electron transport ability, capable ofpreventing the wavelength of light emission from being prolonged, andhaving a high glass transition temperature. Preferred compounds usableas the first organic compound are listed below. In the structuralformulae of the exemplified compounds, R represents a hydrogen atom or asubstituent, and n represents an integer of 3 to 5.

[Second Organic Compound]

In the present invention, a delayed fluorescent material capable ofemitting delayed fluorescence is used as the second organic compound. Inparticular, a thermal activation type delayed fluorescent material thatundergoes reverse intersystem crossing from an excited triplet state toan excited singlet state through absorption of thermal energy ispreferably used. A thermal activation type delayed fluorescent materialcan absorb heat generated by a device to relatively readily undergoreverse intersystem crossing from an excited triplet state to an excitedsinglet state, and can make the excited triplet energy efficientlycontribute toward light emission.

The delayed fluorescent material for use in the present invention ispreferably such that the difference ΔE_(st) between the energy levelE_(s1) in a lowest excited singlet state and the energy level E_(T1) ina lowest excited triplet state at 77 K is 0.3 eV or less, morepreferably 0.2 eV or less, even more preferably 0.1 eV or less, furthermore preferably 0.08 eV or less. The delayed fluorescent material suchthat the energy difference ΔE_(st) thereof falls within the above rangecan relatively readily undergo reverse intersystem crossing from anexcited triplet state to an excited singlet state, and can make theresultant excited triplet energy efficiently contribute toward lightemission.

The delayed fluorescent material usable as the second organic compoundis not specifically limited.

As the delayed fluorescent material for the second organic compound,specifically, compounds represented by the following general formula (1)are preferred.

(A)m-L-(D)n  General Formula (1)

wherein L represents an (m+n)-valent aromatic linking group; Arepresents a group having a positive Hammett's σ_(p) value, or a phenylgroup; D represents a group having a negative Hammett's σ_(p) value(except a phenyl group); m represents an integer of 1 or more; nrepresents an integer of 2 or more; when m is 2 or more, plural A's maybe the same as or different from each other; two of plural D's aregroups containing an aromatic ring common to them, but having adifferent structure.

In the general formula (1), L represents an (m+n)-valent aromaticlinking group, m and n each correspond to the number of A and the numberof D bonding to the aromatic linking group. The aromatic linking grouprepresented by L is formed of an aromatic ring, and among the positionsof the aromatic ring substitutable with a substituent, A is replacedwith the hydrogen atom at the m positions to bond to a carbon atom, andD is replaced with the hydrogen atom at the n positions to bond to acarbon atom. Namely, the aromatic linking group represented by L isformed of an aromatic ring from which (m+n) hydrogen atoms have beenremoved. Among the positions of the aromatic ring substitutable with asubstituent, a part or all of those positions can be substituted with Aor D, but preferably, all the substitutable positions of the aromaticring are substituted with A or D.

The aromatic ring to constitute the aromatic linking group representedby L may be an aromatic ring of a hydrocarbon (hereinafter referred toas “aromatic hydrocarbon ring”), or may also be an aromatic ringcontaining a hetero atom (hereinafter referred to as “aromatic heteroring”). The group substitutable with a substituent of the aromatichydrocarbon ring is a methine group (—CH═), and the group substitutablewith a substituent of the aromatic hetero ring includes a methine group(—CH═) and an imino group (—NH—).

The aromatic hydrocarbon ring to constitute the aromatic linking grouprepresented by L may be a single ring, or may be a condensed ring formedby condensation of 2 or more aromatic hydrocarbon rings, or may be aspiro ring formed of 2 or more aromatic hydrocarbon rings bonding via aspiro bond, or may be a linked ring formed of 2 or more aromatichydrocarbon rings linking together. In the case where 2 or more aromatichydrocarbon rings link together, they may link in a linear manner or ina branched manner. The carbon number of the aromatic hydrocarbon ring toconstitute the aromatic linking group is preferably 6 to 22, morepreferably 6 to 18, even more preferably 6 to 14, further morepreferably 6 to 10. Specific examples of the aromatic hydrocarbon ringto constitute the aromatic linking group include a benzene ring, anaphthalene ring, a biphenyl ring, and a spirofluorene ring.

The aromatic hetero ring to constitute the aromatic linking grouprepresented by L may be a single ring, or may be a condensed ring formedby condensation of one or more hetero rings and an aromatic hydrocarbonring or an aromatic hetero ring, or may be a spiro ring formed of onehetero ring and one aromatic hydrocarbon ring or aromatic hetero ringbonding via a spiro bond, or may be a linked ring formed of one or morearomatic hetero ring and an aromatic hydrocarbon ring or an aromatichetero ring that link together. The carbon number of the aromatic heteroring is preferably 5 to 22, more preferably 5 to 18, even morepreferably 5 to 14, further more preferably 5 to 10. The hetero atom toconstitute the aromatic hetero ring is preferably a nitrogen atom.Specific examples of the aromatic hetero ring include a pyridine ring, apyridazine ring, a pyrimidine ring, a triazole ring, and a benzotriazolering.

More preferably, the aromatic ring to constitute the aromatic linkinggroup represented by L is a benzene ring.

A is a group having a positive Hammett's σ_(p) value, and D is a grouphaving a negative Hammett's σ_(p) value. However, exceptionally, aphenyl group is included in A and is not included in D.

Here, “Hammett's σ_(p) value” is one propounded by L. P. Hammett, and isone to quantify the influence of a substituent on the reaction rate orthe equilibrium of a para-substituted benzene derivative. Specifically,the value is a constant (σ_(p)) peculiar to the substituent in thefollowing equation that is established between a substituent and areaction rate constant or an equilibrium constant in a para-substitutedbenzene derivative:

log(k/k ₀)=ρσ_(p)

or

log(K/K₀)=ρσ_(p)

In the above equations, k represents a rate constant of a benzenederivative not having a substituent; k₀ represents a rate constant of abenzene derivative substituted with a substituent; K represents anequilibrium constant of a benzene derivative not having a substituent;K₀ represents an equilibrium constant of a benzene derivativesubstituted with a substituent; ρ represents a reaction constant to bedetermined by the kind and the condition of reaction. Regarding thedescription relating to the “Hammett's σ_(p) value” and the numericalvalue of each substituent in the present invention, reference may bemade to the description relating to σ_(p) value in Hansch, C. et. al.,Chem. Rev., 91, 165-195 (1991). A group having a negative Hammett's σpvalue tends to exhibit electron-donating performance (donor-likeperformance) and a group having a positive Hammett's σp value tends toexhibit electron-accepting performance (acceptor-like performance).

m A's bond to the aromatic linking group represented by L. m is aninteger of 1 or more, and when m is 2 or more, plural A's may be thesame as or different from each other. The upper limit of m is notspecifically limited, but is preferably smaller than n.

The group having a positive Hammett's σp value represented by Aincludes, though not specifically limited thereto, a cyano group, agroup containing a carbonyl group or a sulfonyl group, or a substitutedor unsubstituted heteroaryl group. The hetero atom that the heteroarylgroup contains includes a nitrogen atom, an oxygen atom, a sulfur atomand a boron atom, and preferably the heteroaryl group contains at leastone nitrogen atom as the ring member. Such a heteroaryl group includes a5-membered or 6-membered ring group containing a nitrogen atom as thering member, or a group having a condensed ring structure of a5-membered or 6-membered ring having a nitrogen atom as the ring memberwith a benzene ring, and is preferably a monovalent group formed byremoving one hydrogen atom from a pyridine ring, a pyrazine ring, apyrimidine ring, a pyridazine ring or a triazine ring, or a group havinga condensed ring structure formed by condensation of these aromatichetero rings, or a group having a condensed ring structure of such anaromatic hetero ring with a benzene ring. In addition, a group having acondensed ring structure of a quinone ring or a pyrone ring with abenzene ring and formed by removing one hydrogen atom from the benzenering thereof is also preferred as a group having a positive Hammett'sσ_(p) value. Here, the benzene ring to be condensed with a quinone ringor a pyrone ring can be substituted with a substituent. In the casewhere the benzene ring condensed with a quinone ring or a pyrone ringhas a substituent and in the case where the heteroaryl group has asubstituent, examples of the substituent in such cases include an alkylgroup having 1 to 20 carbon atoms, an aryl group having 6 to 40 carbonatoms, a cyano group, a halogen atom, and a heteroaryl group having 5 to40 carbon atoms. Of such substituents, those that can be substitutedwith a substituent can be substituted with a substituent. A includes aphenyl group. When m is 2 or more, the number of cyano groups of pluralA's can be, for example, 0 to 2, and is more preferably 1 than 2.

Specific examples of the group having a positive Hammett's σ_(p) valuerepresented by A are shown below. However, in the present invention, thegroup having a positive Hammett's σ_(p) value represented by A shouldnot be limitatively interpreted by these exemplified groups. Among thegroups exemplified below, those having a cyclic structure bond to L byreplacing the hydrogen atom of any one methine group (—CH═) thatconstitutes the cyclic structure with L. The right and left lines of COof the carbonyl group (—CO—) and the right and left lines of SO₂ of thesulfonyl group (—SO₂—) each represent a single bond (chemical bond). Thecarbonyl group (—CO—) and the sulfonyl group (—SO₂—) each directly bondto L via one single bond, or links to L via a linking group, and anatomic group bonds to the other single bond. The atomic group includes asubstituted or unsubstituted alkyl group, aryl group and heteroarylgroup. Preferably, the carbon number of the alkyl group is 1 to 20, thecarbon number of the aryl group is 6 to 40, and the carbon number of theheteroaryl group is 5 to 40.

Next, D is described.

n D's bond to the aromatic linking group represented by L. n is aninteger of 2 or more, and two of plural D's are groups containing anaromatic ring common to them but having a different structure. The typeof the common aromatic ring is not specifically limited, and may be anaromatic hydrocarbon ring or an aromatic hetero ring. Regarding thedescription and the preferred range of the aromatic hydrocarbon ring andthe aromatic hetero ring, reference may be made to the correspondingpart in the description of the following requirements (a) and (b).Though not specifically limited thereto, a preferred aromatic ring is abenzene ring. Also though not specifically limited thereto, preferredexamples of a group containing an aromatic ring include a groupcontaining a diarylamino structure or a carbazolyl structure.Preferably, two of plural D's are both groups having a hetero atom, morepreferably groups containing a nitrogen atom. Specific structures ofthose groups are represented by any of general formulae (2) to (9) to bementioned below.

Preferably, two of plural D's satisfy the following requirement (a) or(b).

Requirement (a)

Two D's both have an aromatic ring that contains an atom bonding to L,and the aromatic ring is common between the two D's, but the two differfrom each other in point of at least one condition of the number of thesubstituents on the aromatic ring, the substitution site of the aromaticring substituted with the substituent, and the structure of thesubstituent on the aromatic ring.

Requirement (b)

Two D's both have a linking group bonding to L and one or more aromaticrings bonding to the linking group, and in the case where the two D'seach have one aromatic ring bonding to the linking group, the linkinggroup and the aromatic ring bonding to the linking group are commonbetween the two D's, but the two differ from each other in point of atleast one condition of the number of the substituents on the aromaticring, the substitution site of the aromatic ring substituted with thesubstituent, and the structure of the substituent on the aromatic ring.In the case where the two D's each have 2 or more aromatic rings bondingto the linking group, the linking group, the number of the aromaticrings bonding to the linking group and the plural aromatic rings arecommon between the two D's, but at least one combination of the aromaticrings common between the two D's differs in point of at least onecondition of the number of the substituents on the aromatic ring, thesubstitution site of the aromatic ring substituted with the substituent,and the structure of the substituent on the aromatic ring.

In the following description, one of the two D's satisfying therequirement (a) or (b) is referred to as “the one D”, and the otherthereof is referred to as “the other D”. Two D's satisfying therequirement (a) or (b) (“the one D” and “the other D”) may be composedof one combination or two or more combinations out of plural D's.

In the requirement (a), the “aromatic ring containing an atom bonding toL” that the one D has is referred to as “the one aromatic ring”, and the“aromatic ring containing an atom bonding to L” that the other D has isreferred to as “the other aromatic ring”.

In the requirement (b) “where the two D's each have 2 or more aromaticrings bonding to the linking group, the linking group, the number of thearomatic rings bonding to the linking group and the plural aromaticrings are common between the two D's, but at least one combination ofthe aromatic rings common between the two D's differs in point of atleast one condition of the number of the substituents on the aromaticring, the substitution site of the aromatic ring substituted with thesubstituent, and the structure of the substituent on the aromatic ring”means that, with reference to an example where a benzene ring and anaphthalene ring link to L via a trivalent linking group in the one D,the two D's differ in point of at least one condition of the number ofthe substituents on the aromatic ring, the substitution site of thearomatic ring substituted with the substituent, and the structure of thesubstituent on the aromatic ring, in a combination of aromatic ringscommon to each other where, also in the other D, a benzene ring and anaphthalene ring link to L via a trivalent linking group like in the oneD, that is, a combination of a benzene ring of the one D and a benzenering of the other D, or a combination of a naphthalene ring of the one Dand a naphthalene ring of the other D, or both these combinations. Inthe requirement (b), in the case where the two D's each have onearomatic ring bonding to a linking group, the “aromatic ring linking tothe linking group” that the one D has is referred to as “the onearomatic ring”, and the “aromatic ring linking to the linking group”that the other D has is referred to as “the other aromatic ring”. In thecase where two D's have two or more aromatic rings bonding to a linkinggroup, one of the “combination of the two aromatic rings common to eachother” differing in at least one substituent condition is referred to as“the one aromatic ring”, and the other is referred to as “the otheraromatic ring”.

In the following description, “the number of the substituents on thearomatic ring”, “the substitution site of the aromatic ring substitutedwith the substituent”, and “the structure of the substituent on thearomatic ring” may be collectively referred to as “the substituentcondition”.

The aromatic ring in the requirements (a) and (b) may be an aromatichydrocarbon ring or an aromatic hetero ring, and may be a single ring ora condensed ring. In the case where the aromatic ring constitutes alinked ring, the aromatic ring on the side nearest to L is the aromaticring referred to in the requirements (a) and (b). Common aromatic ringsmean that the two are completely the same between the one aromatic ringand the other aromatic ring except the number of the hydrogen atomsubstituted with a substituent and the substituent condition. Thelinking group in the requirement (b) may be divalent linking group thatlink L and one aromatic ring, or may be a trivalent or higher linkinggroup that links L and two or more aromatic rings. In the case where thenumber of the aromatic rings bonding to the linking group is 2 or more,the aromatic rings bonding to the linking group may be the same as ordifferent from each other.

The difference in the substituent condition in aromatic rings can bejudged as follows.

First, one D and another D different from the one D are compared inpoint of the number of the substituents on the common aromatic rings(common aromatic rings among the aromatic rings containing an atombonding to L, or common aromatic rings among the aromatic rings linkingto L via a linking group). In the case where the number of thesubstituents differs, it is judged that the two D's differ in point of“the number of the substituents on the aromatic ring” among theabove-mentioned substituent conditions. In the case where the number ofthe substituents is the same, the two are compared in point of the site(substitution site) of the aromatic ring substituted with thesubstituent, and when there is at least one different substitution site,it is judged that the two D's differ in point of “the substitution siteof the aromatic ring substituted with the substituent” among theabove-mentioned substituent conditions. When the substitution sites areall the same, the two are compared in point of the structure of thesubstituent on the aromatic ring. In the case where at least onesubstituent on the aromatic ring of the one D has a different structurefrom that of the substituent in the corresponding substitution site ofthe aromatic ring of the another D, it is judged that the two D's differin point of “the structure of the substituent on the aromatic ring”.Here, “the corresponding substitution site” of the aromatic ring of theanother D is a position common to the substitution site of the aromaticring of the one D in point of the structural formula of the aromaticring, and specifically, when the structural formulae of the aromaticrings of the two D's are laid on each other in all the substitutionsites, the overlapping positions correspond to “the correspondingsubstitution sites”. Otherwise, the positions having a common positionnumber of the aromatic ring given according to the IUPAC nomenclaturesystem correspond to “the corresponding substitution sites”. However, inthe case where the structural formula of an aromatic ring has anaxisymmetric structure, the positions that overlap in 180° rotationaround the symmetrical axis as a center are also judged to be includedin “the corresponding substitution sites”, and in the case where atleast one substituent on an aromatic ring of one D differs from bothsubstituents at the corresponding substitution sites of the aromaticring of another D in point of the structure, it is judged that the twoD's differ in “the structure of the substituent on the aromatic ring”.For example, regarding the substituent at the 3-position of a carbazolering, a case where the substituent of the carbazole ring differs fromboth the substituent at the 3-position and the substituent at the6-position of another carbazole ring corresponds to this case.

“A substituent differing in the structure” means that the substituentdiffers in at least one condition of, for example, the kind of thesubstituent, the kind of the atoms constituting the substituent and thenumber of each constituent atom, the presence or absence of a saturatedbond or the position thereof, the chain-like structure (linearstructure, branched structure, and the branching position in thebranched structure), the cyclic structure (the number of ring members,aromatic or nonaromatic, presence or absence of condensed ring). In thecase where two substituents on an aromatic ring bond to each other toform a cyclic structure, the two substituents can be considered to be“substituent” in the substituent conditions. For example, in the case ofa naphthalene ring as an aromatic ring, the entire naphthalene ring canbe considered as “an aromatic ring”, or the case can be considered to bea benzene ring substituted with a substituent at the neighboringpositions thereof. In the case where a naphthalene ring is considered asa benzene ring substituted with a substituent at the neighboringpositions thereof, the relationship between the naphthalene ring of thetype and an unsubstituted benzene ring is such that the aromatic ring iscommon to the two and the two differ in point of the number of thesubstituents. In the present invention, the case where the targetedaromatic rings are in such a relationship between two D's is also judgedto satisfy the requirement (a) or (b).

Among the substituent conditions, preferably, one aromatic ring differsfrom another aromatic ring in point of the “number of the substituentson the aromatic ring”, and more preferably, one aromatic ring issubstituted with at least one substituent and another aromatic ring isunsubstituted.

Preferably, two D's satisfying the requirement (a) or (b) contain adiarylamine structure (provided that the two aryl groups constitutingthe diarylamine structure may bond to each other). In the presentinvention, the “diarylamine structure” means a structure where two arylgroups bond to a nitrogen atom, and the two aryl groups may bond to eachother, and may be substituted with a substituent. Regarding thepreferred range and specific examples of the substituent in the casewhere the aryl group has a substituent, reference may be made to thepreferred range and specific examples of the substituent that R¹¹ to R¹⁹in the general formula (2) can represent. The aromatic hydrocarbon ringto constitute the aryl group of the diarylamine structure may be asingle ring or a condensed ring formed by condensation of 2 or morearomatic hydrocarbon rings. The carbon number of the aromatichydrocarbon ring to constitute the aryl group of the diarylaminestructure is preferably 6 to 22, more preferably 6 to 18, even morepreferably 6 to 14, further more preferably 6 to 10. Specific examplesof the aryl group of the diarylamine structure include a substituted orunsubstituted phenyl group, and a substituted or unsubstituted naphthylgroup. In the case where two aryl group of the diarylamine structurebond to each other, the two aryl groups may bond via a single bond, ormay link via a linking group. The linking group that links the two arylgroups include an oxygen atom, a sulfur atom, and a substituted orunsubstituted alkylene group. In the case where the alkylene group has asubstituent, the substituent includes a substituted or unsubstitutedalkyl group, and a substituted or unsubstituted aryl group. Specificexamples of the diarylamine structure where two aryl groups bond to eachother include a carbazole structure, a phenoxazine structure, aphenothiazine structure and an acridine structure. More preferably, twoD's satisfying the requirement (a) or (b) contain a carbazole structure.

In the group containing a diarylamine structure, the diarylaminestructure may bond to L via a single bond, or may link to L via adivalent linking group. The divalent linking group is not specificallylimited. The diarylamine structure may bond to L or to a divalentlinking group by substitution of any hydrogen atom of the two arylgroups thereof with L or a divalent linking group, or may bond theretoby bonding of the nitrogen atom of the structure to L or a divalentlinking group. Preferably, the nitrogen atom of the diarylaminestructure bond to L or a divalent linking group, and more preferably,the nitrogen atom of the diarylamine structure directly bond to L (via asingle bond). Specifically, the diarylamine structure is preferably adiarylamino group (provided that the two aryl groups constituting thediarylamine structure may bond to each other), and is more preferably adiarylamino group bonding to L via a single bond.

Here, regarding the relationship between the diarylamine structure andthe requirement (a) or (b), first in the case where the two aryl groupsof the diarylamine structure bond to each other and the one aryl groupor the nitrogen atom bond to L via a single bond, the entire diarylaminestructure corresponds to the aromatic ring in the requirement (a).

In the case where the two aryl groups of the diarylamine structure bondto each other and the one aryl group or the nitrogen atom links to L viaa divalent linking group, the divalent linking group corresponds to thelinking group in the requirement (b) and the entire diarylaminestructure corresponds to the aromatic ring in the requirement (b).

In the case where the two aryl groups of the diarylamine structure donot bond to each other and the one aryl group bond to L via a singlebond, the one aryl group bonding to L via a single bond corresponds tothe aromatic ring in the requirement (a9.

In the case where the two aryl group of the diarylamine structure do notbond to each other and the nitrogen atom bond to L via a single bond,the nitrogen atom bonding to L via a single bond corresponds to thelinking group in the requirement (b), and the two aryl groups correspondto the aromatic ring in the requirement (b).

In the case where the two aryl groups of the diarylamine structure donot bond to each other and the one aryl group links to L via a divalentlinking group, the divalent linking group corresponds to the linkinggroup in the requirement (b) and the one aryl group bonding to thedivalent linking group corresponds to the aromatic ring in therequirement (b).

In the case where the two aryl groups of the diarylamine structure donot bond to each other and the nitrogen atom links to L via a divalentlinking group, the divalent linking group and the nitrogen atomcorrespond to the linking group in the requirement (b), and the two arylgroups correspond to the aromatic ring in the requirement (b).

Preferably, the two D's (“the one D” and “the other D”) satisfying therequirement (a) are groups represented by the following general formula(2).

In the general formula (2), R¹¹ to R¹⁹ each independently represent ahydrogen atom, a substituent or a bonding position to L, one of R¹¹ toR¹⁹ is a bonding position to L. The bonding position to L is preferablyR¹⁹. The number of the substituents is not specifically limited, andamong R¹¹ to R¹⁹, all except the bonding position to L may beunsubstituted (hydrogen atom). In the case where two or more of R¹¹ toR¹⁹ are substituents, the plural substituents may be the the same as ordifferent from each other. However, the group represented by the generalformula (2) to be one D differs from the group represented by thegeneral formula (2) to be the other D in point of at least one conditionof the number of the substituents of R¹¹ to R¹⁹, the position of thesubstituent and the structure of the substituent, so as to satisfy therequirement (a).

For example, preferably, in one D, at least one of R¹¹ to R¹⁸ is asubstituent, and in the other D, one of R¹¹ to R¹⁸ corresponding to thesubstituent in the one D is a hydrogen atom, and more preferably, in oneD, at least one of R¹³ and R¹⁶ is a substituent, and in the other D, onecorresponding to a substituent in the one D of R¹³ and R¹⁶ is a hydrogenatom. Further preferably, in one D, both of R¹³ and R¹⁶ aresubstituents, and even more preferably, both of R¹³ and R¹⁶ aresubstituted or unsubstituted aryl groups. In the other D, even morepreferably, all of R¹¹ to R¹⁸ are hydrogen atoms.

In the following, specific examples of the group represented by thegeneral formula (2) are shown. However, the groups represented by thegeneral formula (2) usable in the present invention are not limitativelyinterpreted by these specific examples. In the groups shown below, thesingle line extending from a benzene ring and not expressed as a linkinggroup to any other atom means a methyl group. In the following groups,the hydrogen atom bonding at 1 to 9-positions of the carbazole ring isreplaced with L to bond to L. Preferably, the bonding position to L inthe carbazole ring is a 9-position. As a combination of two D'ssatisfying the requirement (a), for example, combinations of two groupsselected from the following groups can be employed here.

Also preferably, the two D's (“the one D” and “the other D”) satisfyingthe requirement (a) or (b) are groups represented by any of thefollowing general formulae (3) to (5).

In the general formulae (3) to (5), R²¹ to R³¹, R⁴¹ to R⁵³, and R⁶¹ toR⁷³ each independently represent a hydrogen atom, a substituent, or abonding position to L, one of R²¹ to R³¹, one of R⁴¹ to R⁵³, and one ofR⁶¹ to R⁷³ each are a bonding position to L. The bonding position to Lis preferably R³¹, R⁵³, and R⁷³. In the case where one of R²¹ to R³⁰,one of R⁴¹ to R⁵², and one of R⁶¹ to R⁷² are a bonding position to L,the group represented by any of the general formulae (3) to (5) is tosatisfy the requirement (a). In the case where R³¹, R⁵³, and R⁷³ are abonding position to L, the group represented by any of the generalformulae (3) to (5) is to satisfy the requirement (b), and the nitrogenatom corresponds to the linking group in the requirement (b), and thebenzene ring and the naphthalene ring bonding to the nitrogen atomcorrespond to the aromatic rings in the requirement (b). The number ofthe substituents in the general formulae (3) to (5) is not specificallylimited, and all of R²¹ to R³¹, R⁴¹ to R⁵³, R⁶¹ to R⁶⁷, and R⁶⁸ to R⁷²excepting the bonding position to L can be unsubstituted (hydrogenatom). In the case where the general formulae (3) to (5) each have 2 ormore substituents, the substituents may be the same as or different fromeach other. However, the group represented by any of the generalformulae (3) to (5) to be one D and the group represented by any of thegeneral formulae (3) to (5) to be the other D differ from each other inat least any group of R²¹ to R³¹, R⁴¹ to R⁵³, and R⁶¹ to R⁷³ in point ofat least one condition of the number of the substituents, the positionof the substituent, and the structure of the substituent, so as tosatisfy the requirement (a) or the requirement (b).

In the following, specific examples of the groups represented by any ofthe general formulae (3) to (5) are shown. However, the groupsrepresented by any of the general formulae (3) to (5) usable in thepresent invention are not limitatively interpreted by these specificexamples. In the groups shown below, the single line extending from abenzene ring and not expressed as a linking group to any other atommeans a methyl group. The groups exemplified below bond to L byreplacing the hydrogen atom of any one methine group (—CH═) constitutingthe cyclic structure, or the hydrogen atom bonding to the nitrogen atomwith L. Preferably, the bonding position to L in these groups is thenitrogen atom. As a combination of two D's satisfying the requirement(a) or (b), for example, combinations of two groups selected from thefollowing groups can be employed here.

Also preferably, two D's (“one D” and “the other D”) satisfying therequirement (a) or (b) each are a group represented by the followinggeneral formula (6).

In the general formula (6), R⁸¹ to R⁹⁵ each independently represent ahydrogen atom, a substituent or a bonding position to L, one of R⁸¹ toR⁹⁵ is a bonding position to L. Preferably, R⁸³ is a bonding position toL. In the group represented by the general formula (6), the benzene ringhaving a bonding position to L among the three benzene rings bonding tothe nitrogen atom corresponds to the aromatic ring in the requirement(a). Also, the benzene ring having a bonding position to L and thenitrogen atom can be considered to correspond to the linking group inthe requirement (b) and the remaining two benzene rings can beconsidered to correspond to the aromatic ring in the requirement (b).The number of the substituents is not specifically limited, and amongR⁸¹ to R⁹⁵, all except the bonding position to L can be unsubstituted(hydrogen atom). In the case where two or more of R⁸¹ to R⁹⁵ aresubstituents, the plural substituents may be the same or different fromeach other. However, at least in any group of R⁸¹ to R⁸³, R⁸⁶ to R⁹⁰ andR⁹¹ to R⁹⁵, the group represented by the general formula (6) to be one Dand the group represented by the general formula (6) to be the other Ddiffer from each other in point of at least one condition of the numberof the substituents, the position of the substituent and the structureof the substituent so as to satisfy the requirement (a) or (b).

Also preferably, two D's (“one D” and “the other D”) satisfying therequirement (a) each are a group represented by the following generalformula (7).

In the general formula (7), R¹⁰¹ to R¹⁰⁹ each independently represent ahydrogen atom, a substituent or a bonding position to L, one of R¹⁰¹ toR¹⁰⁹ is a bonding position to L. R¹⁰⁹ is preferably a bonding positionto L. The number of the substituents is not specifically limited, andamong R¹⁰¹ to R¹⁰⁹, all except the bonding position to L can beunsubstituted (hydrogen atom). In the case where two or more of R¹⁰¹ toR¹⁰⁹ are substituents, the plural substituents may be the same ordifferent from each other. However, among R¹⁰¹ to R¹⁰⁹, the grouprepresented by the general formula (7) to be one D and the grouprepresented by the general formula (7) to be the other D differ fromeach other in point of at least one condition of the number of thesubstituents, the position of the substituent and the structure of thesubstituent so as to satisfy the requirement (a).

Also preferably, two D's (“one D” and “the other D”) satisfying therequirement (a) each are a group represented by the following generalformula (8).

In the general formula (8), R¹¹¹ to R¹¹⁹ each independently represent ahydrogen atom, a substituent or a bonding position to L, one of R¹¹¹ toR¹¹⁹ is a bonding position to L. R¹¹⁹ is preferably a bonding positionto L. The number of the substituents is not specifically limited, andamong R¹¹¹ to R¹¹⁹, all except the bonding position to L can beunsubstituted (hydrogen atom). In the case where two or more of R¹¹¹ toR¹¹⁹ are substituents, the plural substituents may be the same ordifferent from each other. However, among R¹¹¹ to R¹¹⁹, the grouprepresented by the general formula (8) to be one D and the grouprepresented by the general formula (8) to be the other D differ fromeach other in point of at least one condition of the number of thesubstituents, the position of the substituent and the structure of thesubstituent so as to satisfy the requirement (a).

Also preferably, two D's (“one D” and “the other D”) satisfying therequirement (a) each are a group represented by the following generalformula (9).

In the general formula (9), R¹²¹ to R¹³¹ each independently represent ahydrogen atom, a substituent or a bonding position to L, one of R¹²¹ toR¹³¹ is a bonding position to L. R¹³¹ is preferably a bonding positionto L. The number of the substituents is not specifically limited, andamong R¹²¹ to R¹³¹, all except the bonding position to L can beunsubstituted (hydrogen atom). In the case where two or more of R¹²¹ toR¹³¹ are substituents, the plural substituents may be the same ordifferent from each other. However, among R¹²¹ to R¹³¹, the grouprepresented by the general formula (9) to be one D and the grouprepresented by the general formula (9) to be the other D differ fromeach other in point of at least one condition of the number of thesubstituents, the position of the substituent and the structure of thesubstituent so as to satisfy the requirement (a).

Examples of the substituents that R¹¹ to R¹⁹ in the general formula (2),R²¹ to R³¹ in the general formula (3), R⁴¹ to R⁵³ in the general formula(4), R⁶¹ to R⁷³ in the general formula (5), R⁸¹ to R⁹⁵ in the generalformula (6), R¹⁰¹ to R¹⁰⁹ in the general formula (7), R¹¹¹ to R¹¹⁹ inthe general formula (8), and R¹²¹ to R¹³¹ in the general formula (9) canrepresent include a hydroxy group, a halogen atom, a cyano group, analkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20carbon atoms, an alkylthio group having 1 to 20 carbon atoms, analkyl-substituted amino group having 1 to 20 carbon atoms, an acyl grouphaving 2 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms,a heteroaryl group having 3 to 40 carbon atoms, an alkenyl group having2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, analkoxy carbonyl group having 2 to 10 carbon atoms, an alkylsulfonylgroup having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10carbon atoms, an amide group, an alkylamide group having 2 to 10 carbonatoms, a trialkylsilyl group having 3 to 20 carbon atoms, atrialkylsilylalkyl group having 4 to 20 carbon atoms, atrialkylsilylalkenyl group having 5 to 20 carbon atoms, atrialkylsilylalkynyl group having 5 to 20 carbon atoms, and a nitrogroup. Among these specific examples, those that can be furthersubstituted with a substituent can be substituted with, for example, asubstituent of these specific examples. More preferred substituents area substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,an alkoxy group having 1 to 20 carbon atoms, a substituted orunsubstituted aryl group having 6 to 40 carbon atoms, a substituted orunsubstituted diarylamino group having 1 to 20 carbon atoms, and asubstituted or unsubstituted carbazolyl group.

Among D's, the other groups than those satisfying the requirement (a) or(b) may be any ones having a negative Hammett's σ_(p) value, and, withno other specific limitations, preferably contain a diarylaminestructure (provided that the two aryl groups constituting thediarylamine structure may bond to each other), more preferably containsa diarylamino group (provided that the two aryl groups constituting thediarylamino group may bond to each other), and are even more preferablyany of the groups represented by the general formulae (2) to (9).Regarding the description, the preferred ranges and the specificexamples of these structures and groups, reference may be made to thedescription, the preferred ranges and the specific examples of thediarylamine structure, the diarylamino group and the groups representedby the general formulae (2) to (9) for the two D's satisfying therequirement (a) or (b). However, regarding these references, thedescription relating to the requirement (a) or (b) is not included inthe matters to be referred to.

Preferably, the compound represented by the general formula (1) is acompound represented by the following general formula (10).

In the general formula (10), A¹ represents a group having a positiveHammett's σ_(p) value. R¹ to R⁵ each represent a hydrogen atom, a grouphaving a positive Hammett's σ_(p) value, or a group having a negativeHammett's σ_(p) value, and at least two of R¹ to R⁵ each are a grouphaving a negative Hammett's σ_(p) value (except a phenyl group). Whenone or more of R¹ to R⁵ each are a group having a positive Hammett'sσ_(p) value, the group having a positive Hammett's σ_(p) valuerepresented by A¹ and the group having a positive Hammett's σ_(p) valueof R¹ to R⁵ may be the same as or different from each other.

Two groups having a negative Hammett's σ_(p) value of R¹ to R⁵preferably satisfy the following requirement (a) or the requirement (b).

Requirement (a)

The two groups having a negative Hammett's σ_(p) value both have anaromatic ring that contains an atom bonding to L, and the aromatic ringis common between the two groups having a negative Hammett's σ_(p)value, but the two differ from each other in point of at least onecondition of the number of the substituents on the aromatic ring, thesubstitution site of the aromatic ring substituted with the substituent,and the structure of the substituent on the aromatic ring.

Requirement (b)

The two groups having a negative Hammett's σ_(p) value both have alinking group bonding to L and one or more aromatic rings bonding to thelinking group, and in the case where the two groups having a negativeHammett's σ_(p) value each have one aromatic ring bonding to the linkinggroup, the linking group and the aromatic ring bonding to the linkinggroup are common between the two groups having a negative Hammett'sσ_(p) value, but the two differ from each other in point of at least onecondition of the number of the substituents on the aromatic ring, thesubstitution site of the aromatic ring substituted with the substituent,and the structure of the substituent on the aromatic ring. In the casewhere the two groups having a negative Hammett's σ_(p) value each have 2or more aromatic rings bonding to the linking group, the linking group,the number of the aromatic rings bonding to the linking group and theplural aromatic rings are common between the two groups having anegative Hammett's σ_(p) value, but at least one combination of thearomatic rings common between the two groups having a negative Hammett'sσ_(p) value differs in point of at least one condition of the number ofthe substituents on the aromatic ring, the substitution site of thearomatic ring substituted with the substituent, and the structure of thesubstituent on the aromatic ring.

Regarding the description, the preferred ranges and the specificexamples of the group having a positive Hammett's σ_(p) valuerepresented by A¹ and R¹ to R⁵, the group having a negative Hammett'sσ_(p) value represented by R¹ to R⁵, and the two groups having anegative Hammett's σ_(p) value of R¹ to R⁵, and regarding thedescription of the requirements (a) and (b), reference may be made tothe description, the preferred ranges and the specific examples of thegroup having a positive Hammett's σ_(p) value represented by A in thegeneral formula (1), the group having a negative Hammett's σ_(p) valuerepresented by D, and two of the plural D's, as well as to thedescription relating to the requirements (a) and (b) given hereinabove.

Preferably, the number of the groups having a positive Hammett's σ_(p)value of R¹ to R⁵ is 0 to 3, more preferably 0 to 2, even morepreferably 0 or 1, and most preferably 0. Preferably, the number of thegroups having a negative Hammett's σ_(p) value of R¹ to R⁵ is 2 to 5,more preferably 3 to 5, even more preferably 4 or 5, and most preferably5. Among R¹ to R⁵, the number of a combination of two groups satisfyingthe requirement (a) or the requirement (b) may be 1 or 2. Preferably,the combination of the two groups satisfying the requirement (a) or therequirement (b) is a combination of those in a point-symmetric positionrelative to the benzene ring in the general formula (10). Specifically,it is preferable that one or both of a combination of R¹ and R⁴ and acombination of R² and R⁵ satisfy the requirement (a) or the requirement(b).

The compound represented by the general formula (1) is also preferably acompound represented by the following general formula (11).

In the general formula (11), A^(X1) represents a group having a positiveHammett's σ_(p) value. R^(X11) to R^(X14) each represent a hydrogenatom, a group having a positive Hammett's σ_(p) value, or a group havinga negative Hammett's σ_(p) value, and at least two of R^(X11) to R^(X14)each are a group having a negative Hammett's σ_(p) value (except aphenyl group). When one or more of R^(X11) to R^(X14) each are a grouphaving a positive Hammett's σ_(p) value, the group having a positiveHammett's σ_(p) value represented by A^(X1) and the group having apositive Hammett's σ_(p) value of R^(X11) to R^(X14) may be the same asor different from each other.

Two groups having a negative Hammett's σ_(p) value of R^(X11) to R^(X14)preferably satisfy the above-mentioned requirement (a) or requirement(b).

Regarding the description, the preferred ranges and the specificexamples of the group having a positive Hammett's σ_(p) valuerepresented by A^(X1) and R^(X11) to R^(X14), the group having anegative Hammett's σ_(p) value represented by R^(X11) to R^(X14), andthe two groups having a negative Hammett's σ_(p) value of R^(X11) toR^(X14), and regarding the description of the requirements (a) and (b),reference may be made to the description, the preferred ranges and thespecific examples of the group having a positive Hammett's σ_(p) valuerepresented by A in the general formula (1), the group having a negativeHammett's σ_(p) value represented by D, and two of the plural D's, aswell as to the description relating to the requirements (a) and (b)given hereinabove.

Preferably, the number of the groups having a positive Hammett's σ_(p)value of R^(X11) to R^(X14) is 0 to 2, more preferably 0 or 1, and mostpreferably 0. Preferably, the number of the groups having a negativeHammett's σ_(p) value of R^(X11) to R^(X14) is 2 to 4, more preferably 3or 4, even more preferably 4. Among R^(X11) to R^(X14), the number of acombination of two groups satisfying the requirement (a) or therequirement (b) may be 1 or 2.

Also preferably, the second organic compound is a compound representedby the following general formula (12). An organic electroluminescentdevice produced using the compound represented by the general formula(12) as a second organic compound can have an enhanced light emissionefficiency and a prolonged lifetime.

In the general formula (12), at least three of R¹¹ to R¹⁵ are selectedfrom a substituted or unsubstituted diarylamino group (provided that thetwo aryl groups constituting the diarylamino group may bond to eachother) and a halogen atom, and all the selected groups are not the same,and at least one is a substituted or unsubstituted diarylaminogroup(provided that the two aryl groups constituting the diarylaminogroup may bond to each other), and the remaining 0 to 2 each represent ahydrogen atom, a substituted or unsubstituted aryl group, or a cyanogroup.

For example, the compound can include a case where at least three of R¹¹to R¹⁵ each are a substituted or unsubstituted amino group and some ofR¹¹ to R¹⁵ each are a halogen atom. In that case, all the substituted orunsubstituted diarylamino group existing in the molecule are not thesame. The compound can also include a case where at least two of R¹¹ toR¹⁵ each are a substituted or unsubstituted diarylamino group and atleast one of R¹¹ to R¹⁵ is a halogen atom. In that case, all thesubstituted or unsubstituted diarylamino group existing in the moleculecan be the same or can be different. In still another case of thecompound, at least one of R¹¹ to R¹⁵ is a substituted or unsubstituteddiarylamino group and at least two of R¹¹ to R¹⁵ each are a halogenatom. In that case, all the halogen atoms existing in the molecule canbe the same or can be different.

Regarding the description and the preferred range of the diarylaminogroup that R¹¹ to R¹⁵ can represent, reference may be made to thedescription and the preferred range of the diarylamine structure thatthe two D's satisfying the above-mentioned requirement (a) or (b) canrepresent. Regarding the specific structure, reference may be made tothe description relating to the above-mentioned general formulae (2) to(5) an (7) to (9). Here, R¹⁹ in the general formula (2), R³¹ in thegeneral formula (3), R⁴¹ in the general formula (4), R⁷³ in the generalformula (5), R¹⁰⁹ in the general formula (7), R¹¹⁹ in the generalformula (8), and R¹³¹ in the general formula (9) each are a bondingposition. In particular, the diarylamino group that R¹¹ to R¹⁵ canrepresent is preferably a group represented by the general formula (2)(where R¹⁹ is a bonding position).

The substituent with which the two aryl groups to constitute thediarylamino group for R¹¹ to R¹⁵ can be substituted is preferably asubstituted or unsubstituted aryl group, a substituted or unsubstitutedheteroaryl group, a substituted or unsubstituted diarylamino group, asubstituted or unsubstituted diheteroaryl amino group, a substituted orunsubstituted arylheteroarylamino group, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted alkoxy group, or asubstituted or unsubstituted aryloxy group. These groups can be furthersubstituted with any of these substituents.

Specific examples of the substituted diarylamino group that R¹¹ to R¹⁵can represent include a 3-methylcarbazol-9-yl group, a3,6-dimethylcarbazol-9-yl group, a 3-ethylcarbazol-9-yl group, a3,6-diethylcarbazol-9-yl group, a 3-t-butylcarbazol-9-yl group, a3,6-di-t-butylcarbazol-9-yl group, a 3-phenylcarbazol-9-yl group, a3.6-diphenylcarbazol-9-yl group, a 3-(carbazol-9-yl)carbazol-9-yl group,and a 3.6-bis(carbazol-9-yl)carbazol-9-yl group.

When R¹¹ to R¹⁵ each are a substituted or unsubstituted carbazol-9-ylgroup, preferably the substituted or unsubstituted carbazol-9-yl groupis not substituted with a substituted or unsubstituted diarylamino groupin point of the light emission efficiency and the lifetime of organicelectroluminescent devices. The substituent for the carbazol-9-yl groupis preferably a substituted or unsubstituted aryl group, a substitutedor unsubstituted heteroaryl group, a substituted or unsubstituteddiarylamino group, a substituted or unsubstituted diheteroaryl aminogroup, a substituted or unsubstituted arylheteroarylamino group, asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedalkoxy group, or a substituted or unsubstituted aryloxy group.

In the case where the compound has two or more substituted orunsubstituted diarylamino groups in the molecule and where the groupsdiffer, the number of the kinds of the substituted or unsubstituteddiarylamino groups existing in the molecule is preferably 2 or 3, morepreferably 2. For example, in the case where three of R¹¹ to R¹⁵ eachare a substituted or unsubstituted diarylamino group, preferably, two ofthese are the same and one differs. Examples thereof include a casewhere R¹¹ and R¹⁵ are the same and R¹² differs, a case where R¹¹ and R¹⁴are the same and R¹² differs, a case where R¹² and R¹⁴ are the same andR¹⁵ differs, and a case where R¹² and R¹⁴ are the same and R¹¹ differs.For example, in the case where four of R¹¹ to R¹⁵ each are a substitutedor unsubstituted diarylamino group, preferably, three of them are thesame and one differs or two of them are the same and the other two arethe same. Examples thereof include a case where R¹¹ and R¹⁵ are the sameand R¹² and R¹⁴ are the same, a case where R¹¹ and R¹² are the same andR¹⁴ and R¹⁵ are the same, a case where R¹¹ and R¹⁴ are the same and R¹²and R¹⁵ are the same, a case where R¹² and R¹⁴ and R¹⁵ are the same andR¹¹ alone differs, and a case where R¹¹ and R¹⁴ and R¹⁵ are the same andR¹² alone differs. In the case where all of R¹¹ to R¹⁵ each are asubstituted or unsubstituted diarylamino group, preferably, four of themare the same and one differs, or three are the same and two differ.Examples thereof include R¹¹ and R¹³ and R¹⁵ are the same and R¹² andR¹⁴ are the same, a case where R¹¹ and R¹² and R¹³ are the same and R¹⁴and R¹⁵ are the same, a case where R¹² and R¹³ and R¹⁴ are the same andR¹¹ and R¹⁵ are the same, and a case where R¹¹ and R¹² and R¹⁴ are thesame and R¹³ and R¹⁵ are the same.

In the case where the compound has two or more different kinds ofsubstituted or unsubstituted diarylamino groups in the molecule, thedifference may be a difference whether or not the diarylamino group hasa substituent, or may be a difference in the point of the kind of thesubstituent bonding to the diarylamino group, or may be a difference inthe point of the bonding site of the substituent bonding to thediarylamino group. Preferred is a difference whether or not thediarylamino group has a substituent, or a difference in the point of thekind of the substituent bonding to the diarylamino group. One example ofthe difference in the point of the kind of the substituent bonding tothe diarylamino group is an embodiment having a carbazol-9-yl groupsubstituted with an alkyl group and a carbazol-9-yl group substitutedwith an aryl group in the molecule. One example of the difference in thepoint of the bonding site of the substituent bonding to the diarylaminogroup is an embodiment having a carbazol-9-yl group substituted with analkyl group at the 3-position and the 6-position and a carbazol-9-ylgroup substituted with an alkyl group at the 3-position alone in themolecule.

The halogen atom that R¹¹ to R¹⁵ can represent may be any of a fluorineatom, a chlorine atom, a bromine atom and an iodine atom, but ispreferably a fluorine atom.

The remaining 0 to 2 of R¹¹ to R¹⁵ each represent a hydrogen atom, asubstituted or unsubstituted aryl group or a cyano group. Preferred is asubstituted or unsubstituted aryl group, or a cyano group. In the casewhere the compound has such remaining R¹¹ to R¹⁵ (that is, when thenumber of the remaining groups is 1 or 2), the remaining group may beany of R¹¹ to R¹⁵, but preferably includes at least one of R¹², R¹³ andR¹⁴, more preferably one or two of R¹², R¹³ and R¹⁴, even morepreferably the remaining group at least includes R¹³. Regarding thedescription and the preferred range of the aryl group that the remainingone of R¹¹ to R¹⁵ can represent, reference may be made to thedescription and the preferred range of the aryl group of the diarylaminestructure that the two D's satisfying the above-mentioned requirement(a) or (b) can represent. The aryl group that the remaining R¹¹ to R¹⁵can represent may be substituted, and the substituent is preferably analkyl group or an aryl group. The aryl group that the remaining R¹¹ toR¹⁵ can represent includes, for example, a phenyl group substituted withan alkyl group or an aryl group at the 4-position, or a phenyl groupsubstituted with an alkyl group or an aryl group at the 3-position andthe 5-position.

A preferred compound group of the compounds represented by the generalformula (12) is a group of compounds of the formula where at least threeof R¹¹ to R¹⁵ each are a substituted or unsubstituted diarylamino group,and none of R¹¹ to R¹⁵ is a halogen atom.

A preferred compound group of the compounds represented by the generalformula (12) is a group of compounds of the formula where at least threeof R¹¹ to R¹⁵ each are a substituted or unsubstituted carbazol-9-ylgroup. Among these, a more preferred compound group is a group of thecompounds where all the carbazol-9-yl groups existing in the moleculeare not substituted with a substituted or unsubstituted diarylaminogroup (provided that the two aryl groups constituting the diarylaminogroup may bond to each other, and, for example, a carbazol-9-yl group isincluded). The compounds of the type are preferred in point of the lightemission efficiency and the lifetime, as compared with compounds havinga carbazol-9-yl group substituted with a substituted or unsubstituteddiarylamino group. A group of the compounds of the type includescompounds represented by the following general formula (13).

In the general formula (13), at least three of R¹¹ to R¹⁵ each representa substituted or unsubstituted carbazol-9-yl group, and all these atleast three substituted or unsubstituted carbazol-9-yl groups are notthe same, and are not substituted with a substituted or unsubstituteddiarylamino group (provided that the two aryl groups constituting thediarylamino group may bond to each other), the remaining 0 to 2 eachrepresent a hydrogen atom, a substituted or unsubstituted aryl group, ahalogen atom, or a cyano group.

Among the compounds represented by the general formula (13), forexample, a group of compounds in which the remaining 0 to 2 each are asubstituted or unsubstituted aryl group or a cyano group can beselected, and further, a group of compounds in which the remaining 0 to2 each are a substituted or unsubstituted aryl group can also beselected.

Among the compound represented by the general formula (13), for example,a group of compounds in which R¹³ is a hydrogen atom, a substituted orunsubstituted aryl group, a halogen atom or a cyano group, or a group ofcompounds in which R¹³ is a hydrogen atom, a substituted orunsubstituted aryl group or a cyano group, or a group of compounds inwhich R¹³ is a substituted or unsubstituted aryl group, or a cyanogroup, or a group of compounds in which R¹³ is a substituted orunsubstituted aryl group can also be selected.

Among the compounds represented by the general formula (13), a group ofcompounds in which at least three of R¹¹ to R¹⁵ each represent asubstituted carbazol-9-yl group, and at least any one substituent ofthose groups (one substituent of the carbazol-9-yl groups) differs canalso be selected.

Among the compounds represented by the general formula (13), a group ofcompounds in which at least one of R¹¹ to R¹⁵ is a substitutedcarbazol-9-yl group, and at least one of R¹¹ to R¹⁵ is an unsubstitutedcarbazol-9-yl group can also be selected.

Among the compounds represented by the general formula (13), a group ofcompounds in which R¹¹ and R¹⁵ are the same, a group of compounds inwhich R¹² and R¹⁴ are the same, a group of compounds in which R¹¹ andR¹² and R¹⁵ are the same, and a group of compounds in which R¹¹ and R¹²and R¹⁴ are the same can also be selected.

Also preferably, the second organic compound is a compound representedby the following general formula (14).

In the general formula (14), at least three of R¹¹, R¹², R¹⁴ and R¹⁵ areselected from a substituted or unsubstituted diarylamino group (providedthat the two aryl groups constituting the diarylamino group may bond toeach other) and a halogen atom, and all the selected groups are not thesame, and at least one is a substituted or unsubstituted diarylaminogroup(provided that the two aryl groups constituting the diarylaminogroup may bond to each other), and the remaining 0 to 1 represents ahydrogen atom, a substituted or unsubstituted aryl group, or a cyanogroup.

Regarding the description and the preferred ranges of R¹¹, R¹², R¹⁴ andR¹⁵ in the general formula (14), reference may be made to thecorresponding description of the general formula (12).

A group of specific compounds usable as a delayed fluorescent materialfor the second organic compound includes, for example, a group ofcompounds represented by the following general formula.

In the general formula (15), R¹ and R² each independently represent asubstituted or unsubstituted carbazolyl group, a substituted orunsubstituted aryl group, a substituted or unsubstituted heteroarylgroup, a substituted or unsubstituted alkyl group, or a substituted orunsubstituted cycloalkyl group, R⁵ and R⁶ each independently represent asubstituted or unsubstituted alkyl group, R⁷, R⁸ and R⁹ eachindependently represent a substituted or unsubstituted aryl group, asubstituted or unsubstituted alkyl group, or a substituted orunsubstituted carbazolyl group, R¹⁰ represents a carbazolyl group, andthe carbazolyl group may be substituted with a substituted orunsubstituted carbazolyl group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted heteroaryl group, a substituted orunsubstituted alkyl group, or a substituted or unsubstituted cycloalkylgroup, n1, n2, n6 and n7 each independently represent an integer of anyof 0 to 4, n5 represents an integer of any of 0 to 3, n8 and n9 eachindependently represent an integer of any of 0 to 5. n10 represents 0 or1, and when n1, n2 and n5 to n9 each are an integer of 2 or more, pluralR¹'s, R²'s and R⁵'s to R⁹'S corresponding to n1, n2 and n5 to n9,respectively, each may be the same as or different from each other.

Regarding the detailed description and the preferred range of thegeneral formula (15), and regarding specific examples of the compound,reference may be made to the relating description in WO2014/051184 thatis referred to herein as a part of the present description.

Specific examples of a group of other compounds usable as a delayedfluorescent material for the second organic compound include, forexample, a group of compounds represented by the following generalformula.

D-A-D  General Formula (16)

In the general formula (16), A represents a divalent group having astructure represented by any of the following general formulae (2-a) to(5-a) (provided that the hydrogen atom in the structure of the generalformulae (2-a) to (5-a) may be substituted with a substituent).

In the general formula (16), two D's each independently represent agroup having a structure selected from the following group (providedthat the hydrogen atom in the structure may be substituted with asubstituent).

Regarding the detailed description and the preferred range of thegeneral formula (16), and regarding specific examples of the compound,reference may be made to the relating description in WO2014/126200 thatis referred to herein as a part of the present description.

Specific examples of a group of other compounds usable as a delayedfluorescent material for the second organic compound include, forexample, a group of compounds represented by the following generalformula.

In the general formula (17), R¹, R³ and R⁵ each represent a cyano group,or R¹, R², R⁴ and R⁵ each represent a cyano group, and the remaining R¹to R⁶ each independently represent a group represented by any of thefollowing general formula (2-b) to (8-b).

In the general formulae (2-b) to (8-b), L¹² to L¹⁸ each represent asingle bond, or a substituted or unsubstituted arylene group, *represents a bonding position to the benzene ring in the general formula(1). R¹¹ to R²⁰, R²¹ to R²⁸, R³¹ to R³⁸, R^(3a), R^(3b), R⁴¹ to R⁴⁸,R^(4a), R⁵¹ to R⁵⁸, R⁶¹ to R⁶⁸, and R⁷¹ to R⁷⁸ each independentlyrepresent a hydrogen atom or a substituent. R¹¹ and R¹², R¹² and R¹³,R¹³ and R¹⁴, R¹⁴ and R¹⁵, R¹⁶ and R¹⁷, R¹⁷ and R¹⁸, R¹⁸ and R¹⁹, R¹⁹ andR²⁰, R²¹ and R²², R²² and R²³, R²³ and R²⁴, R²⁴ and R²⁵, R²⁵ and R²⁶,R²⁶ and R²⁷, R²⁷ and R²⁸, R³¹ and R³², R³² and R³³, R³³ and R³⁴, R³⁵ andR³⁶, R³⁶ and R³⁷, R³⁷ and R³⁸, R^(3a) and R^(3b), R⁴¹ and R⁴², R⁴² andR⁴³, R⁴³ and R⁴⁴, R⁴⁵ and R⁴⁶, R⁴⁶ and R⁴⁷, R⁴⁷ and R⁴⁸, R⁵¹ and R⁵²,R⁵² and R⁵³, R⁵³ and R⁵⁴, R⁵⁵ and R⁵⁶, R⁵⁶ and R⁵⁷, R⁵⁷ and R⁵⁸, R⁶¹ andR⁶², R⁶² and R⁶³, R⁶³ and R⁶⁴, R⁶⁵ and R⁶⁶, R⁶⁶ and R⁶⁷, R⁶⁷ and R⁶⁸,R⁷¹ and R⁷², R⁷² and R⁷³, R⁷³ and R⁷⁴, R⁷⁵ and R⁷⁶, R⁷⁶ and R⁷⁷, and R⁷⁷and R⁷⁸ each may bond to each other to form a cyclic structure.

Regarding the detailed description, the preferred range and specificexamples of the compound of the general formula (17), reference may bemade to the relating description in WO2015/129715 that is referred toherein as a part of the present description.

Specific examples of a group of other compounds usable as a delayedfluorescent material for the second organic compound include, forexample, a group of compounds represented by the following generalformula.

In the general formula (18), Ar¹ to Ar³ each independently represent asubstituted or unsubstituted aryl group, and at least one of Ar¹ to Ar³is independently a carbazolyl group substituted with a group containingan electron-attracting group at the N-position.

Regarding the detailed description and the preferred range of thegeneral formula (18) and specific examples of the compound thereof,reference may be made to the relating description in WO2015/133501 thatis referred to herein as a part of the present description.

Specific examples of a group of other compounds usable as a delayedfluorescent material for the second organic compound include, forexample, a group of compounds represented by the following generalformula.

In the general formula (19), m and n each independently represent aninteger of 1 to 3, m+n is 2 to 4; A represents an electron-donatingsubstituted heteroaryl group, and at least one substituent on thearomatic hetero ring is an electron-attracting group; and when m is 2 ormore, plural A's may be the same or different.

Regarding the detailed description and the preferred range of thegeneral formula (19) and specific examples of the compound thereof,reference may be made to the relating description in WO2015/137136 thatis referred to herein as a part of the present description.

Specific examples of a group of other compounds usable as a delayedfluorescent material for the second organic compound include, forexample, a group of compounds represented by the following generalformula.

In the general formula (20), the ring A represents an aromatic ringrepresented by the following formula (1a) that is condensed with theneighboring ring at an arbitrary position, the ring B represents ahetero ring represented by the following formula (1b) that is condensedwith the neighboring ring at an arbitrary position. Ar in the formulae(20) and (1b) independently represents an aromatic hydrocarbon group oran aromatic heterocyclic group. R in the formulae (20) and (1a)independently represents a hydrogen atom or a monovalent substituent,and the neighboring substituents may integrally form a ring, nrepresents an integer of 1 or more and 4 or less.

Regarding the detailed description and the preferred range of thegeneral formula (20) and specific examples of the compound thereof,reference may be made to the relating description in JP 5124785 that isreferred to herein as a part of the present description.

Specific examples of a group of other compounds usable as a delayedfluorescent material for the second organic compound include, forexample, a group of compounds represented by the following generalformula.

In the general formula (21), R¹ to R⁵ each independently represent ahydrogen atom or a substituent, one of R¹ to R⁵ is a cyano group, one tothree of R¹ to R⁵ each are an aryl group Ar optionally substituted withan alkyl group or an aryl group (in which the benzene ring to constitutethe aryl group Ar may be condensed with a ring that may optionallycontain an oxygen atom or a sulfur atom in addition to carbon atoms as aring skeleton-constituting atom, but is not condensed with a ringcontaining any other hetero atom than an oxygen atom and a sulfur atomas a ring skeleton-constituting atom), and when two or more of R¹ to R⁵are Ar's, these Ar's may be the same as or different from each other,one to three of R¹ to R⁵ each are a donor group D (but excepting onethat corresponds to Ar), and when two or more of R¹ to R⁵ are D's, theseD's may be the same as or different from each other.

In the general formula (21), preferably, R¹ to R⁵ each are independentlya cyano group, Ar or D; D preferably contains a substituted amino group;and D is preferably a group represented by the following general formula(2c).

In the general formula (2c), R¹¹ and R¹² each independently represent asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedalkenyl group, a substituted or unsubstituted aryl group, or asubstituted or unsubstituted heteroaryl group. L represents a singlebond, a substituted or unsubstituted arylene group, or a substituted orunsubstituted heteroarylene group. * indicates a bonding position to thecarbon atom (C) constituting a ring skeleton of the benzene ring in thegeneral formula (21). R¹¹ and R¹² may bond to each other to form acyclic structure.

D is preferably a group represented by the following general formula(3c).

In the general formula (3c), R²¹ to R²⁸ each independently represent ahydrogen atom or a substituent. L represents a single bond, asubstituted or unsubstituted arylene group, or a substituted orunsubstituted heteroarylene group. R²¹ and R²², R²² and R²³, R²³ andR²⁴, R²⁴ and R²⁵, R²⁶ and R²⁷, and R²⁷ and R²⁸ each may bond to eachother to form a linking group necessary for forming a cyclic structure.R²⁵ and R²⁶ may bond to each other to form a single bond or a linkinggroup.

D is preferably a group represented by the following general formula(4c).

In the general formula (4c), R³¹ to R⁴⁰ each independently represent ahydrogen atom or a substituent. L represents a single bond, asubstituted or unsubstituted arylene group, or a substituted orunsubstituted heteroarylene group. R³¹ and R³², R³² and R³³, R³³ andR³⁴, R³⁴ and R³⁵, R³⁶ and R³⁷, R³⁷ and R³⁸, R³⁸ and R³⁹, and R³⁹ and R⁴⁰each may bond to each other to form a linking group necessary forforming a cyclic structure. R³⁵ and R³⁶ may bond to each other to form asingle bond or a linking group. * indicates a bonding position to thecarbon atom (C) constituting the ring skeleton of the benzene ring inthe general formula (21).

L is preferably a single bond. Also preferably, R³ is a cyano group andL is a substituted or unsubstituted phenylene group. D is preferably agroup represented by any of the following general formulae (5c) to (8c).

In the general formulae (5c) to (8c), R⁴¹ to R⁴⁶, R⁵¹ to R⁶⁰, R⁶¹ toR⁶⁸, and R⁷¹ to R⁷⁸ each independently represent a hydrogen atom or asubstituent. L¹¹ to L¹⁴ each independently represent a single bond, asubstituted or unsubstituted arylene group, or a substituted orunsubstituted heteroarylene group. In the general formula (8c), Xrepresents an oxygen atom, a sulfur atom, a substituted or unsubstitutednitrogen atom, a substituted or unsubstituted carbon atom, a substitutedor unsubstituted silicon atom or a carbonyl group, which is divalent andwhich has a linking chain length of one atom, or represents asubstituted or unsubstituted ethylene group, a substituted orunsubstituted vinylene group, a substituted or unsubstituted o-arylenegroup or a substituted or unsubstituted o-heteroarylene group, which isdivalent and which has a bonding chain length of two atoms.

Regarding the detailed description and the preferred range of thegeneral formula (21) and specific examples of the compound thereof,reference may be made to the relating description in PCT/JP2018/024302and a laid-open publication thereof that are referred to herein as apart of the present description.

Specific examples of a group of other compounds usable as a delayedfluorescent material for the second organic compound include, forexample, a group of compounds represented by the following generalformula.

In the general formula (22), R¹ to R⁵ each independently represent ahydrogen atom or a substituent, 0 to 3 of R¹ to R⁵ each are an arylgroup Ar optionally substituted with an alkyl group or an aryl group (inwhich the benzene ring to constitute the aryl group Ar may be condensedwith a ring that may optionally contain an oxygen atom or a sulfur atomin addition to carbon atoms as a ring skeleton-constituting atom, but isnot condensed with a ring containing any other hetero atom than anoxygen atom and a sulfur atom as a ring skeleton-constituting atom), andwhen two or more of R¹ to R⁵ are Ar's, these Ar's may be the same as ordifferent from each other, 1 to 4 of R¹ to R⁵ each are an acceptor groupA (but excepting one that corresponds to Ar), and when two or more of R¹to R⁵ are A's, these A's may be the same as or different from eachother, 1 to 4 of R¹ to R⁵ each are a donor group D (but excepting onethat corresponds to Ar), and when two or more of R¹ to R⁵ are D's, theseD's may be the same as or different from each other.

Preferably, 1 to 3 of R¹ to R⁵ in the general formula (22) each are anaryl group Ar optionally substituted with an alkyl group or an arylgroup; R³ is preferably an acceptor group A; R¹ and R⁵ each arepreferably a donor group D; the donor group D is preferably asubstituted or unsubstituted diarylamino group (in which the two arylgroups constituting the diarylamino group may bond to each other);preferably, the donor group D is a substituted or unsubstituteddiarylamino group and the two aryl groups constituting the diarylaminogroup bond to each other; preferably, the acceptor group A is asubstituted or unsubstituted heteroaryl group; preferably, the acceptorgroup A is a heteroaryl group containing a nitrogen atom as a ringskeleton constituting atom; and preferably the acceptor group A is anaryl-substituted heteroaryl group.

Regarding the detailed description and the preferred range of thegeneral formula (22) and specific examples of the compound thereof,reference may be made to the relating description in Japanese PatentApplication No. 2017-168885 and a laid-open publication thereof that arereferred to herein as a part of the present description.

Specific examples of compounds usable as the second organic compound areshown below. In the specific examples, the compounds 1 to 7 arespecifically described in the following Tables and the structuralformulae thereof are also shown below. The compound 8 and after that arespecifically described only in the following Tables. However, thecompounds represented by the general formula (1) usable in the presentinvention should not be limitatively interpreted by these specificexamples.

In the following Tables, specific examples of compounds represented bythe following general formula (10) or general formula (11) are shown.The general formula (2a) and the general formula (2b) representing thesubstituents in the general formula (10) and the general formula (11)are also shown below.

TABLE 1-1 Compound General formula (10) No. A¹ R¹ R² R³ R⁴ R⁵  1 CNGeneral formula (2a) General formula (2b) General formula (2a) Generalformula (2b) General formula (2a)  2 CN General formula (2a) Generalformula (2b) General formula (2a) General formula (2b) General formula(2a)  3 CN General formula (2a) General formula (2b) General formula(2a) General formula (2b) General formula (2a)  4 CN General formula(2a) General formula (2a) General formula (2a) General formula (2b)General formula (2a)  5 CN General formula (2a) General formula (2a)General formula (2a) General formula (2b) General formula (2a)  6 CNGeneral formula (2a) General formula (2a) General formula (2a) Generalformula (2b) General formula (2a)  7 CN General formula (2a) Generalformula (2b) General formula (2a) General formula (2b) General formula(2a)  8 CN General formula (2a) General formula (2b) General formula(2a) General formula (2b) General formula (2a)  9 CN General formula(2a) General formula (2b) General formula (2a) General formula (2b)General formula (2a)  10 CN General formula (2a) General formula (2b)General formula (2a) General formula (2b) General formula (2a)  11 CNGeneral formula (2a) General formula (2b) General formula (2a) Generalformula (2b) General formula (2a)  12 CN General formula (2a) Generalformula (2b) General formula (2a) General formula (2b) General formula(2a)  13 CN General formula (2a) General formula (2b) General formula(2a) General formula (2b) General formula (2a)  14 CN General formula(2a) General formula (2b) General formula (2a) General formula (2b)General formula (2a)  15 CN General formula (2a) General formula (2b)General formula (2a) General formula (2b) General formula (2a)  16 CNGeneral formula (2a) General formula (2b) General formula (2a) Generalformula (2b) General formula (2a)  17 CN General formula (2a) Generalformula (2b) General formula (2a) General formula (2b) General formula(2a)  18 CN General formula (2a) General formula (2b) General formula(2a) General formula (2b) General formula (2a)  19 CN General formula(2a) General formula (2b) General formula (2a) General formula (2b)General formula (2a)  20 CN General formula (2a) General formula (2b)General formula (2a) General formula (2b) General formula (2a)  21 CNGeneral formula (2a) General formula (2b) General formula (2a) Generalformula (2b) General formula (2a)  22 CN General formula (2a) Generalformula (2b) General formula (2a) General formula (2b) General formula(2a)  23 CN General formula (2a) General formula (2b) General formula(2a) General formula (2b) General formula (2a)  24 CN General formula(2a) General formula (2b) General formula (2a) General formula (2b)General formula (2a)  25 CN General formula (2a) General formula (2b)General formula (2a) General formula (2b) General formula (2a)  26 CNGeneral formula (2a) General formula (2b) General formula (2a) Generalformula (2b) General formula (2a)  27 CN General formula (2a) Generalformula (2b) General formula (2a) General formula (2b) General formula(2a)  28 CN General formula (2a) General formula (2b) General formula(2a) General formula (2b) General formula (2a)  29 CN General formula(2a) General formula (2b) General formula (2a) General formula (2b)General formula (2a)  30 CN General formula (2a) General formula (2b)General formula (2a) General formula (2b) General formula (2a)  31 CNGeneral formula (2a) General formula (2b) General formula (2a) Generalformula (2b) General formula (2a)  32 CN General formula (2a) Generalformula (2b) General formula (2a) General formula (2b) General formula(2a)  33 CN General formula (2a) General formula (2b) General formula(2a) General formula (2b) General formula (2a)  34 CN General formula(2a) General formula (2b) General formula (2a) General formula (2b)General formula (2a)  35 CN General formula (2a) General formula (2b)Phenyl General formula (2b) General formula (2a)  36 CN General formula(2a) General formula (2b) Phenyl General formula (2b) General formula(2a)  37 CN General formula (2a) General formula (2b) Phenyl Generalformula (2b) General formula (2a)  38 CN General formula (2a) Generalformula (2b) Phenyl General formula (2b) General formula (2a)  39 CNGeneral formula (2a) General formula (2b) Phenyl General formula (2b)General formula (2a)  40 CN General formula (2a) General formula (2b)Phenyl General formula (2b) General formula (2a)  41 CN General formula(2a) General formula (2b) Phenyl General formula (2b) General formula(2a)  42 CN General formula (2a) General formula (2b) Phenyl Generalformula (2b) General formula (2a)  43 CN General formula (2a) Generalformula (2b) Phenyl General formula (2b) General formula (2a)  44 CNGeneral formula (2a) General formula (2b) Phenyl General formula (2b)General formula (2a)  45 CN General formula (2a) General formula (2b)Phenyl General formula (2b) General formula (2a)  46 CN General formula(2a) General formula (2b) Phenyl General formula (2b) General formula(2a)  47 CN General formula (2a) General formula (2b) Phenyl Generalformula (2b) General formula (2a)  48 CN General formula (2a) Generalformula (2b) Phenyl General formula (2b) General formula (2a)  49 CNGeneral formula (2a) General formula (2b) Phenyl General formula (2b)General formula (2a)  50 CN General formula (2a) General formula (2b)Phenyl General formula (2a) General formula (2a)  51 CN General formula(2a) General formula (2b) Phenyl General formula (2a) General formula(2a)  52 CN General formula (2a) General formula (2b) Phenyl Generalformula (2a) General formula (2a)  53 CN General formula (2a) Generalformula (2b) H General formula (2b) General formula (2a)  54 CN Generalformula (2a) General formula (2b) H General formula (2b) General formula(2a)  55 CN General formula (2a) General formula (2b) H General formula(2b) General formula (2a)  56 CN General formula (2a) General formula(2b) H General formula (2b) General formula (2a)  57 CN General formula(2a) General formula (2b) H General formula (2b) General formula (2a) 58 CN General formula (2a) General formula (2b) H General formula (2b)General formula (2a)  59 CN CN General formula (2a) General formula (2a)General formula (2b) General formula (2b)  60 CN CN General formula (2a)General formula (2a) General formula (2b) General formula (2b)  61 CN CNGeneral formula (2a) General formula (2a) General formula (2b) Generalformula (2b)  62 CN CN General formula (2a) General formula (2a) Generalformula (2b) General formula (2b)  63 CN CN General formula (2a) Generalformula (2b) General formula (2a) General formula (2b)  64 CN CN Generalformula (2a) General formula (2b) General formula (2a) General formula(2b)  65 CN CN General formula (2a) General formula (2b) General formula(2a) General formula (2b)  66 CN CN General formula (2a) General formula(2b) General formula (2a) General formula (2b)  67 CN CN General formula(2a) General formula (2b) General formula (2b) General formula (2a)  68CN CN General formula (2a) General formula (2b) General formula (2b)General formula (2a)  69 CN CN General formula (2a) General formula (2b)General formula (2b) General formula (2a)  70 CN CN General formula (2a)General formula (2b) General formula (2b) General formula (2a)  71 CN CNGeneral formula (2a) General formula (2b) General formula (2b) Generalformula (2a)  72 CN CN General formula (2a) General formula (2b) Generalformula (2b) General formula (2a)  73 CN CN General formula (2a) Generalformula (2b) General formula (2b) General formula (2a)  74 CN CN Generalformula (2a) General formula (2b) General formula (2b) General formula(2a)  75 CN CN General formula (2a) General formula (2b) General formula(2b) General formula (2a)  76 CN General formula (2a) CN General formula(2a) General formula (2b) General formula (2b)  77 CN General formula(2a) CN General formula (2a) General formula (2b) General formula (2a) 78 CN General formula (2a) CN General formula (2a) General formula (2b)General formula (2a)  79 CN General formula (2a) CN General formula (2a)General formula (2b) General formula (2a)  80 CN General formula (2a) CNGeneral formula (2b) General formula (2a) General formula (2a)  81 CNGeneral formula (2a) CN General formula (2b) General formula (2a)General formula (2a)  82 CN General formula (2a) CN General formula (2b)General formula (2a) General formula (2a)  83 CN General formula (2a) CNGeneral formula (2b) General formula (2a) General formula (2a)  84 CNGeneral formula (2a) CN General formula (2b) General formula (2a)General formula (2a)  85 CN General formula (2a) CN General formula (2b)General formula (2a) General formula (2a)  86 CN General formula (2a) CNGeneral formula (2b) General formula (2a) General formula (2a)  87 CNGeneral formula (2a) CN General formula (2b) General formula (2a)General formula (2a)  88 CN General formula (2a) CN General formula (2b)General formula (2a) General formula (2a)  89 CN General formula (2a) CNGeneral formula (2b) General formula (2a) General formula (2a)  90 CNGeneral formula (2a) CN General formula (2b) General formula (2b)General formula (2a)  91 CN General formula (2a) CN General formula (2b)General formula (2b) General formula (2a)  92 CN General formula (2a) CNGeneral formula (2b) General formula (2b) General formula (2a)  93 CNGeneral formula (2a) CN General formula (2b) General formula (2b)General formula (2a)  94 CN General formula (2a) CN General formula (2b)H General formula (2a)  95 CN General formula (2a) CN General formula(2b) H General formula (2a)  96 CN General formula (2a) CN Generalformula (2b) H General formula (2a)  97 CN General formula (2a) CNGeneral formula (2b) H General formula (2a)  98 CN General formula (2a)CN General formula (2b) H General formula (2a)  99 CN General formula(2a) CN General formula (2b) H General formula (2a) 100 CN Generalformula (2a) General formula (2a) CN General formula (2b) Generalformula (2a) 101 CN General formula (2a) General formula (2a) CN Generalformula (2b) General formula (2a) 102 CN General formula (2a) Generalformula (2a) CN General formula (2b) General formula (2a) 103 CN Generalformula (2a) General formula (2a) CN General formula (2b) Generalformula (2a) 104 CN General formula (2a) General formula (2b) CN Generalformula (2a) General formula (2a) 105 CN General formula (2a) Generalformula (2b) CN General formula (2a) General formula (2a) 106 CN Generalformula (2a) General formula (2b) CN General formula (2a) Generalformula (2a) 107 CN General formula (2a) General formula (2b) CN Generalformula (2a) General formula (2a) 108 CN General formula (2a) Generalformula (2b) CN General formula (2a) General formula (2a) 109 CN Generalformula (2a) General formula (2b) CN General formula (2b) Generalformula (2a) 110 CN General formula (2a) General formula (2b) CN Generalformula (2b) General formula (2a) 111 CN General formula (2a) Generalformula (2b) CN General formula (2b) General formula (2a) 112 CN Generalformula (2a) General formula (2b) CN General formula (2b) Generalformula (2a) 113 CN General formula (2a) CN General formula (2b) CNGeneral formula (2a) 114 CN General formula (2a) CN General formula (2b)CN General formula (2a) 115 CN General formula (2a) CN General formula(2b) CN General formula (2a) 116 CN General formula (2a) CN Generalformula (2b) CN General formula (2a) 117 CN General formula (2a) CNGeneral formula (2b) CN General formula (2a) 118 CN General formula (2a)CN General formula (2b) CN General formula (2a) 119 CN General formula(2a) CN General formula (2b) CN General formula (2a) 120 CN Generalformula (2a) CN General formula (2b) CN General formula (2a) 121 CNGeneral formula (2a) CN General formula (2b) CN General formula (2a) 122CN General formula (2a) CN General formula (2b) CN General formula (2a)123 CN General formula (2a) CN General formula (2b) CN General formula(2a) 124 CN General formula (2a) CN General formula (2b) CN Generalformula (2a) 125 CN Phenyl General formula (2a) General formula (2b)General formula (2a) Phenyl 126 CN Phenyl General formula (2a) Generalformula (2b) General formula (2a) Phenyl 127 CN Phenyl General formula(2a) General formula (2b) General formula (2a) Phenyl 128 CN PhenylGeneral formula (2a) General formula (2b) General formula (2a) Phenyl129 CN Phenyl General formula (2a) General formula (2b) General formula(2a) Phenyl 130 CN Phenyl General formula (2a) General formula (2b)General formula (2a) Phenyl 131 CN Phenyl General formula (2a) Generalformula (2b) General formula (2a) Phenyl 132 CN Phenyl General formula(2a) General formula (2b) General formula (2a) Phenyl 133 CN Generalformula (2a) Phenyl General formula (2b) Phenyl General formula (2a) 134CN General formula (2a) Phenyl General formula (2b) Phenyl Generalformula (2a) 135 CN General formula (2a) Phenyl General formula (2b)Phenyl General formula (2a) 136 CN General formula (2a) Phenyl Generalformula (2b) Phenyl General formula (2a) 137 CN General formula (2a)Phenyl General formula (2b) Phenyl General formula (2a) 138 CN Generalformula (2a) Phenyl General formula (2b) Phenyl General formula (2a) 139CN General formula (2a) Phenyl General formula (2b) Phenyl Generalformula (2a) 140 CN General formula (2a) Phenyl General formula (2b)Phenyl General formula (2a) 141 CN General formula (2a) Phenyl Generalformula (2b) Phenyl General formula (2a) 142 CN General formula (2a)Phenyl General formula (2b) Phenyl General formula (2a) 143 CN Generalformula (2a) Phenyl General formula (2b) Phenyl General formula (2a) 144CN General formula (2a) Phenyl General formula (2b) Phenyl Generalformula (2a) 145 CN General formula (2a) General formula (2b) Generalformula (2b) General formula (2b) General formula (2a) 146 CN Generalformula (2a) General formula (2b) General formula (2b) General formula(2b) General formula (2a) 147 CN General formula (2a) General formula(2b) General formula (2b) General formula (2b) General formula (2a) 148CN General formula (2a) General formula (2b) General formula (2b)General formula (2b) General formula (2a) 149 CN General formula (2a)General formula (2b) Phenyl General formula (2b) General formula (2a)150 CN General formula (2a) General formula (2b) H General formula (2b)General formula (2a) 151 CN General formula (2a) General formula (2b)m,m-DPP*2 General formula (2b) General formula (2a) 152 CN Generalformula (2a) General formula (2b) Phenyl General formula (2b) Generalformula (2a) Compound General formula (2a) No. Ra¹ Ra² Ra³ Ra⁴ Ra⁵ Ra⁶ 1 H H H H H H  2 H H H H H H  3 H H H H H H  4 H H H H H H  5 H H H H HH  6 H H H H H H  7 H H H H H H  8 H H H H H H  9 H H H H H H  10 H H HH H H  11 H H H H H H  12 H H H H H H  13 H H H H H H  14 H H H H H H 15 H H H H H H  16 H H H H H H  17 H H CH₃ H H CH₃  18 H H CH₃ H H CH₃ 19 H H CH₃ H H CH₃  20 H H tert-C₄H₉ H H tert-C₄H₉  21 H H Phenyl H HPhenyl  22 H H H H H H  23 H H Phenyl H H Phenyl  24 H H H H H H  25 H HH H H H  26 H H H H H H  27 H H H H H H  28 H H H H H H  29 H H H H H H 30 H H H H H H  31 H H H H H H  32 H H H H H H  33 H H H H H H  34 H HH H H H  35 H H H H H H  36 H H H H H H  37 H H H H H H  38 H H H H H H 39 H H H H H H  40 H H H H H H  41 H H H H H H  42 H H H H H H  43 H HH H H H  44 H H H H H H  45 H H CH₃ H H CH₃  46 H H CH₃ H H CH₃  47 H HCH₃ H H CH₃  48 H H Phenyl H H Phenyl  49 H H Phenyl H H Phenyl  50 H HH H H H  51 H H H H H H  52 H H H H H H  53 H H H H H H  54 H H H H H H 55 H H H H H H  56 H H H H H H  57 H H H H H H  58 H H H H H H  59 H HH H H H  60 H H H H H H  61 H H H H H H  62 H H CH₃ H H CH₃  63 H H H HH H  64 H H H H H H  65 H H H H H H  66 H H CH₃ H H CH₃  67 H H H H H H 68 H H H H H H  69 H H H H H H  70 H H CH₃ H H CH₃  71 H H CH₃ H H CH₃ 72 H H CH₃ H H CH₃  73 H H tert-C⁴H⁹ H H tert-C⁴H⁹  74 H H tert-C⁴H⁹ HH tert-C⁴H⁹  75 H H Phenyl H H Phenyl  76 H H H H H H  77 H H H H H H 78 H H H H H H  79 H H CH₃ H H CH₃  80 H H H H H H  81 H H H H H H  82H H H H H H  83 H H CH₃ H H CH₃  84 H H CH₃ H H CH₃  85 H H CH₃ H H CH₃ 86 H H tert-C₄H₉ H H tert-C₄H₉  87 H H tert-C₄H₉ H H tert-C₄H₉  88 H HPhenyl H H Phenyl  89 H H Phenyl H H Phenyl  90 H H H H H H  91 H H H HH H  92 H H H H H H  93 H H CH₃ H H CH₃  94 H H H H H H  95 H H H H H H 96 H H H H H H  97 H H CH₃ H H CH₃  98 H H tert-C₄H₉ H H tert-C₄H₉  99H H Phenyl H H Phenyl 100 H H H H H H 101 H H H H H H 102 H H H H H H103 H H CH₃ H H CH₃ 104 H H H H H H 105 H H H H H H 106 H H H H H H 107H H CH₃ H H CH₃ 108 H H CH₃ H H CH₃ 109 H H H H H H 110 H H H H H H 111H H H H H H 112 H H CH₃ H H CH₃ 113 H H H H H H 114 H H H H H H 115 H HH H H H 116 H H CH₃ H H CH₃ 117 H H H H H H 118 H H H H H H 119 H H H HH H 120 H H CH₃ H H CH₃ 121 H H H H H H 122 H H H H H H 123 H H H H H H124 H H CH₃ H H CH₃ 125 H H H H H H 126 H H CH₃ H H CH₃ 127 H H CH₃ H HCH₃ 128 H H tert-C₄H₉ H H tert-C₄H₉ 129 H H tert-C₄H₉ H H tert-C₄H₉ 130H H tert-C₄H₉ H H tert-C₄H₉ 131 H H Phenyl H H Phenyl 132 H H Phenyl H HPhenyl 133 H H H H H H 134 H H H H H H 135 H H H H H H 136 H H CH₃ H HCH₃ 137 H H CH₃ H H CH₃ 138 H H CH₃ H H CH₃ 139 H H tert-C₄H₉ H Htert-C₄H₉ 140 H H tert-C₄H₉ H H tert-C₄H₉ 141 H H tert-C₄H₉ H Htert-C₄H₉ 142 H H Phenyl H H Phenyl 143 H H Phenyl H H Phenyl 144 H HPhenyl H H Phenyl 145 H H H H H H 146 H H CH₃ H H CH₃ 147 H H tert-C₄H₉H H tert-C₄H₉ 148 H H Phenyl H H Phenyl 149 H H Phenyl H H Phenyl 150 HH H H H H 151 H H H H H H 152 H H H H H H Compound General formula (2a)General formula (2b) No. Ra⁷ Ra⁸ Ra⁹ Rb¹ Rb² Rb³  1 H H *1 H H CH₃  2 HH *1 H H tert-C₄H₉  3 H H *1 H H Phenyl  4 H H *1 H H CH₃  5 H H *1 H Htert-C₄H₉  6 H H *1 H H Phenyl  7 H H *1 H H 9-Carbazoly1  8 H H *1 H Hiso-Butyl  9 H H *1 H H 2-Ethylhexyl  10 H H *1 H H Trimehylsilyl  11 HH *1 H H CH₃  12 H H *1 H H Phenyl  13 H H *1 H H CH₃  14 H H *1 H H CH₃ 15 H H *1 H H Dipheylamino  16 H H *1 H H Dipheylamino  17 H H *1 H H H 18 H H *1 H H tert-C₄H₉  19 H H *1 H H Phenyl  20 H H *1 H H CH₃  21 HH *1 H H CH₃  22 H H *1 H H Phenyl  23 H H *1 H H H  24 H H *1 CH₃ H H 25 H H *1 H CH₃ H  26 H H *1 H H H  27 H H *1 H H H  28 H H *1 H H H 29 H H *1 H H H  30 H H *1 H H H  31 H H *1 H H H  32 H H *1 CH₃ H CH₃ 33 H H *1 H CH₃ CH₃  34 H H *1 CH₃ H H  35 H H *1 H H Phenyl  36 H H *1H H CH₃  37 H H *1 H H tert-C₄H₉  38 H H *1 H H tert-C₄H₉  39 H H *1 H H2-Phenylphenyl  40 H H *1 H H 3-Phenylphenyl  41 H H *1 H H4-Phenylphenyl  42 H H *1 H H 2-Phenylphenyl  43 H H *1 H H3-Phenylphenyl  44 H H *1 H H 4-Phenylphenyl  45 H H *1 H H H  46 H H *1H H tert-C₄H₉  47 H H *1 H H tert-C₄H₉  48 H H *1 H H H  49 H H *1 H HCH₃  50 H H *1 H H 2-Phenylphenyl  51 H H *1 H H 3-Phenylphenyl  52 H H*1 H H 4-Phenylphenyl  53 H H *1 H H CH₃  54 H H *1 H H tert-C₄H₉  55 HH *1 H H Phenyl  56 H H *1 H H 2-Phenylphenyl  57 H H *1 H H3-Phenylphenyl  58 H H *1 H H 4-Phenylphenyl  59 H H *1 H H CH₃  60 H H*1 H H tert-C₄H₉  61 H H *1 H H Phenyl  62 H H *1 H H Phenyl  63 H H *1H H CH₃  64 H H *1 H H tert-C₄H₉  65 H H *1 H H Phenyl  66 H H *1 H HPhenyl  67 H H *1 H H CH₃  68 H H *1 H H tert-C₄H₉  69 H H *1 H H Phenyl 70 H H *1 H H H  71 H H *1 H H tert-C₄H₉  72 H H *1 H H Phenyl  73 H H*1 H H H  74 H H *1 H H CH₃  75 H H *1 H H H  76 H H *1 H H CH₃  77 H H*1 H H tert-C₄H₉  78 H H *1 H H Phenyl  79 H H *1 H H Phenyl  80 H H *1H H CH₃  81 H H *1 H H tert-C₄H₉  82 H H *1 H H Phenyl  83 H H *1 H H H 84 H H *1 H H tert-C₄H₉  85 H H *1 H H Phenyl  86 H H *1 H H H  87 H H*1 H H CH₃  88 H H *1 H H H  89 H H *1 H H CH₃  90 H H *1 H H CH₃  91 HH *1 H H tert-C₄H₉  92 H H *1 H H Phenyl  93 H H *1 H H Phenyl  94 H H*1 H H CH₃  95 H H *1 H H tert-C₄H₉  96 H H *1 H H Phenyl  97 H H *1 H HH  98 H H *1 H H H  99 H H *1 H H H 100 H H *1 H H CH₃ 101 H H *1 H Htert-C₄H₉ 102 H H *1 H H Phenyl 103 H H *1 H H Phenyl 104 H H *1 H H CH₃105 H H *1 H H tert-C₄H₉ 106 H H *1 H H Phenyl 107 H H *1 H H tert-C₄H₉108 H H *1 H H Phenyl 109 H H *1 H H CH₃ 110 H H *1 H H tert-C₄H₉ 111 HH *1 H H Phenyl 112 H H *1 H H Phenyl 113 H H *1 H H CH₃ 114 H H *1 H Htert-C₄H₉ 115 H H *1 H H Phenyl 116 H H *1 H H Phenyl 117 H H *1 H H CH₃118 H H *1 H H tert-C₄H₉ 119 H H *1 H H Phenyl 120 H H *1 H H Phenyl 121H H *1 H H CH₃ 122 H H *1 H H tert-C₄H₉ 123 H H *1 H H Phenyl 124 H H *1H H Phenyl 125 H H *1 H H Phenyl 126 H H *1 H H H 127 H H *1 H H Phenyl128 H H *1 H H H 129 H H *1 H H CH₃ 130 H H *1 H H Phenyl 131 H H *1 H HH 132 H H *1 H H CH₃ 133 H H *1 H H CH₃ 134 H H *1 H H tert-C₄H₉ 135 H H*1 H H Phenyl 136 H H *1 H H H 137 H H *1 H H tert-C₄H₉ 138 H H *1 H HPhenyl 139 H H *1 H H H 140 H H *1 H H CH₃ 141 H H *1 H H Phenyl 142 H H*1 H H H 143 H H *1 H H CH₃ 144 H H *1 H H tert-C₄H₉ 145 H H *1 H H CH₃146 H H *1 H H H 147 H H *1 H H H 148 H H *1 H H H 149 H H *1 H H H 150H H *1 H H CH₃ 151 H H *1 H H Phenyl 152 H H *1 H H Phenyl CompoundGeneral formula (2b) No. Rb⁴ Rb⁵ Rb⁶ Rb⁷ Rb⁸ Rb⁹  1 H H CH₃ H H *1  2 HH tert-C₄H₉ H H *1  3 H H Phenyl H H *1  4 H H CH₃ H H *1  5 H Htert-C₄H₉ H H *1  6 H H Phenyl H H *1  7 H H 9-Carbazoly1 H H *1  8 H Hiso-Butyl H H *1  9 H H 2-Ethylhexyl H H *1  10 H H Trimehylsilyl H H *1 11 H H H H H *1  12 H H H H H *1  13 H H tert-C₄H₉ H H *1  14 H HPhenyl H H *1  15 H H Dipheylamino H H *1  16 H H H H H *1  17 H H H H H*1  18 H H tert-C₄H₉ H H *1  19 H H Phenyl H H *1  20 H H CH₃ H H *1  21H H CH₃ H H *1  22 H H H H H *1  23 H H H H H *1  24 H H H H CH₃ *1  25H H H CH₃ H *1  26 H H H H tert-C₄H₉ *1  27 H H H tert-C₄H₉ H *1  28 H HH H Phenyl *1  29 H H H Phenyl H *1  30 CH₃ CH₃ H H H *1  31 PhenylPhenyl H H H *1  32 H H CH₃ H CH₃ *1  33 H H CH₃ CH₃ H *1  34 CH₃ CH₃ HH CH₃ *1  35 H H H H H *1  36 H H CH₃ H H *1  37 H H tert-C₄H₉ H H *1 38 H H tert-C₄H₉ H H *1  39 H H 2-Phenylphenyl H H *1  40 H H3-Phenylphenyl H H *1  41 H H 4-Phenylphenyl H H *1  42 H H Phenyl H H*1  43 H H Phenyl H H *1  44 H H Phenyl H H *1  45 H H H H H *1  46 H Htert-C₄H₉ H H *1  47 H H Phenyl H H *1  48 H H H H H *1  49 H H CH₃ H H*1  50 H H Phenyl H H *1  51 H H Phenyl H H *1  52 H H Phenyl H H *1  53H H CH₃ H H *1  54 H H tert-C₄H₉ H H *1  55 H H Phenyl H H *1  56 H HPhenyl H H *1  57 H H Phenyl H H *1  58 H H Phenyl H H *1  59 H H CH₃ HH *1  60 H H tert-C₄H₉ H H *1  61 H H Phenyl H H *1  62 H H Phenyl H H*1  63 H H CH₃ H H *1  64 H H tert-C₄H₉ H H *1  65 H H Phenyl H H *1  66H H Phenyl H H *1  67 H H CH₃ H H *1  68 H H tert-C₄H₉ H H *1  69 H HPhenyl H H *1  70 H H H H H *1  71 H H tert-C₄H₉ H H *1  72 H H Phenyl HH *1  73 H H H H H *1  74 H H CH₃ H H *1  75 H H H H H *1  76 H H CH₃ HH *1  77 H H tert-C₄H₉ H H *1  78 H H Phenyl H H *1  79 H H Phenyl H H*1  80 H H CH₃ H H *1  81 H H tert-C₄H₉ H H *1  82 H H Phenyl H H *1  83H H H H H *1  84 H H tert-C₄H₉ H H *1  85 H H Phenyl H H *1  86 H H H HH *1  87 H H CH₃ H H *1  88 H H H H H *1  89 H H CH₃ H H *1  90 H H CH₃H H *1  91 H H tert-C₄H₉ H H *1  92 H H Phenyl H H *1  93 H H Phenyl H H*1  94 H H CH₃ H H *1  95 H H tert-C₄H₉ H H *1  96 H H Phenyl H H *1  97H H H H H *1  98 H H H H H *1  99 H H H H H *1 100 H H CH₃ H H *1 101 HH tert-C₄H₉ H H *1 102 H H Phenyl H H *1 103 H H Phenyl H H *1 104 H HCH₃ H H *1 105 H H tert-C₄H₉ H H *1 106 H H Phenyl H H *1 107 H Htert-C₄H₉ H H *1 108 H H Phenyl H H *1 109 H H CH₃ H H *1 110 H Htert-C₄H₉ H H *1 111 H H Phenyl H H *1 112 H H Phenyl H H *1 113 H H CH₃H H *1 114 H H tert-C₄H₉ H H *1 115 H H Phenyl H H *1 116 H H Phenyl H H*1 117 H H CH₃ H H *1 118 H H tert-C₄H₉ H H *1 119 H H Phenyl H H *1 120H H Phenyl H H *1 121 H H CH₃ H H *1 122 H H tert-C₄H₉ H H *1 123 H HPhenyl H H *1 124 H H Phenyl H H *1 125 H H Phenyl H H *1 126 H H H H H*1 127 H H Phenyl H H *1 128 H H H H H *1 129 H H CH₃ H H *1 130 H HPhenyl H H *1 131 H H H H H *1 132 H H CH₃ H H *1 133 H H CH₃ H H *1 134H H tert-C₄H₉ H H *1 135 H H Phenyl H H *1 136 H H H H H *1 137 H Htert-C₄H₉ H H *1 138 H H Phenyl H H *1 139 H H H H H *1 140 H H CH₃ H H*1 141 H H Phenyl H H *1 142 H H H H H *1 143 H H CH₃ H H *1 144 H Htert-C₄H₉ H H *1 145 H H CH₃ H H *1 146 H H H H H *1 147 H H H H H *1148 H H H H H *1 149 H H H H H *1 150 H H CH₃ H H *1 151 H H Phenyl H H*1 152 H H Phenyl H H *1 In the Tables, the general formula (2a) and thegeneral formula (2b) are synonymous with the general formula (2). *1Thislinks to the benzene corresponding to D in the general formula(1).*2“m,m-DPP” is m,m-diphenylphenyl.

TABLE 2-1 General Compound General formula (10) formula (2a) No. A¹ R¹R² R³ R⁴ R⁵ Ra¹ Ra² 153 CN General formula (2a) D1  CN General formula(2a) D1  H H 154 CN General formula (2a) D2  CN General formula (2a) D2 H H 155 CN General formula (2a) D3  CN General formula (2a) D3  H H 156CN General formula (2a) D4  CN General formula (2a) D4  H H 157 CNGeneral formula (2a) D5  CN General formula (2a) D5  H H 158 CN Generalformula (2a) D6  CN General formula (2a) D6  H H 159 CN General formula(2a) D7  CN General formula (2a) D7  H H 160 CN General formula (2a) D8 CN General formula (2a) D8  H H 161 CN General formula (2a) D9  CNGeneral formula (2a) D9  H H 162 CN General formula (2a) D10 CN Generalformula (2a) D10 H H 163 CN General formula (2a) D11 CN General formula(2a) D11 H H 164 CN General formula (2a) D12 CN General formula (2a) D12H H 165 CN General formula (2a) D13 CN General formula (2a) D13 H H 166CN General formula (2a) D14 CN General formula (2a) D14 H H 167 CNGeneral formula (2a) D15 CN General formula (2a) D15 H H 168 CN Generalformula (2a) D16 CN General formula (2a) D16 H H 169 CN General formula(2a) D17 CN General formula (2a) D17 H H 170 CN General formula (2a) D18CN General formula (2a) D18 H H 171 CN General formula (2a) D19 CNGeneral formula (2a) D19 H H 172 CN General formula (2a) D20 CN Generalformula (2a) D20 H H 173 CN General formula (2a) D21 CN General formula(2a) D21 H H 174 CN General formula (2a) D22 CN General formula (2a) D22H H 175 CN General formula (2a) D23 CN General formula (2a) D23 H H 176CN General formula (2a) D24 CN General formula (2a) D24 H H 177 CNGeneral formula (2a) D25 CN General formula (2a) D25 H H 178 CN Generalformula (2a) D26 CN General formula (2a) D26 H H 179 CN General formula(2a) D27 CN General formula (2a) D27 H H 180 CN General formula (2a) D28CN General formula (2a) D28 H H 181 CN General formula (2a) D29 CNGeneral formula (2a) D29 H H 182 CN General formula (2a) D30 CN Generalformula (2a) D30 H H 183 CN General formula (2a) D31 CN General formula(2a) D31 H H 184 CN General formula (2a) D31 CN General formula (2a) D31H H 185 CN General formula (2a) D31 CN General formula (2a) D31 H H 186CN General formula (2a) D31 CN General formula (2a) D31 H H 187 CNGeneral formula (2a) D31 CN General formula (2a) D31 H H 188 CN Generalformula (2a) D31 CN General formula (2a) D31 H H 189 CN General formula(2a) D31 CN General formula (2a) D31 H H 190 CN General formula (2a) D31CN General formula (2a) D31 H H 191 CN General formula (2a) D39 CNGeneral formula (2a) D39 H H 192 CN General formula (2a) D40 CN Generalformula (2a) D40 H H 193 CN General formula (2a) D41 CN General formula(2a) D41 H H 194 CN General formula (2a) D42 CN General formula (2a) D42H H 195 CN General formula (2a) D43 CN General formula (2a) D43 H H 196CN General formula (2a) D44 CN General formula (2a) D44 H H 197 CNGeneral formula (2a) D45 CN General formula (2a) D45 H H 198 CN Generalformula (2a) D46 CN General formula (2a) D46 H H 199 CN General formula(2a) D47 CN General formula (2a) D47 H H 200 CN General formula (2a) D48CN General formula (2a) D48 H H 201 CN General formula (2a) D49 CNGeneral formula (2a) D49 H H 202 CN General formula (2a) D50 CN Generalformula (2a) D50 H H 203 CN General formula (2a) D51 CN General formula(2a) D51 H H 204 CN General formula (2a) D52 CN General formula (2a) D52H H 205 CN General formula (2a) D53 CN General formula (2a) D53 H H 206CN General formula (2a) D54 CN General formula (2a) D54 H H 207 CNGeneral formula (2a) D55 CN General formula (2a) D55 H H 208 CN Generalformula (2a) D56 CN General formula (2a) D56 H H 209 CN General formula(2a) D57 CN General formula (2a) D57 H H 210 CN General formula (2a) D58CN General formula (2a) D58 H H 211 CN General formula (2a) D59 CNGeneral formula (2a) D59 H H 212 CN General formula (2a) D60 CN Generalformula (2a) D60 H H 213 CN General formula (2a) D24 Phenyl D24 Generalformula (2a) H H 214 CN General formula (2a) D24 Phenyl D24 Generalformula (2a) H H 215 CN General formula (2a) D24 Phenyl D24 Generalformula (2a) H H 216 CN General formula (2a) D24 Phenyl D24 Generalformula (2a) H H 217 CN General formula (2a) D24 D11 Phenyl Generalformula (2a) H H 218 CN General formula (2a) D24 D11 Phenyl Generalformula (2a) H H 219 CN General formula (2a) D24 D11 Phenyl Generalformula (2a) H H 220 CN CN D24 General formula (2a) General formula (2a)D24 H H 221 CN CN D24 General formula (2a) General formula (2a) D24 H H222 CN CN D24 General formula (2a) General formula (2a) D24 H H 223 CNCN D24 General formula (2a) General formula (2a) D24 H H 224 CN CN D24D24 D24 General formula (2a) H H 225 CN General formula (2a) CN D24General formula (2a) D24 H H 226 CN General formula (2a) CN Generalformula (2a) D24 General formula (2a) H H 227 CN D24 General formula(2a) CN D24 General formula (2a) H H 228 CN D24 General formula (2a) CND24 General formula (2a) H H 229 CN D24 General formula (2a) CN D24General formula (2a) H H 230 CN D24 General formula (2a) CN D24 Generalformula (2a) H H Compound General formula (2a) No. Ra³ Ra⁴ Ra⁵ Ra⁶ Ra⁷Ra⁸ Ra⁹ 153 CH₃ H H CH₃ H H *1 154 CH₃ H H CH₃ H H *1 155 CH₃ H H CH₃ HH *1 156 CH₃ H H CH₃ H H *1 157 CH₃ H H CH₃ H H *1 158 CH₃ H H CH₃ H H*1 159 CH₃ H H CH₃ H H *1 160 CH₃ H H CH₃ H H *1 161 CH₃ H H CH₃ H H *1162 CH₃ H H CH₃ H H *1 163 CH₃ H H CH₃ H H *1 164 CH₃ H H CH₃ H H *1 165CH₃ H H CH₃ H H *1 166 CH₃ H H CH₃ H H *1 167 CH₃ H H CH₃ H H *1 168 CH₃H H CH₃ H H *1 169 CH₃ H H CH₃ H H *1 170 CH₃ H H CH₃ H H *1 171 CH₃ H HCH₃ H H *1 172 CH₃ H H CH₃ H H *1 173 CH₃ H H CH₃ H H *1 174 CH₃ H H CH₃H H *1 175 CH₃ H H CH₃ H H *1 176 CH₃ H H CH₃ H H *1 177 CH₃ H H CH₃ H H*1 178 CH₃ H H CH₃ H H *1 179 CH₃ H H CH₃ H H *1 180 CH₃ H H CH₃ H H *1181 CH₃ H H CH₃ H H *1 182 CH₃ H H CH₃ H H *1 183 CH₃ H H CH₃ H H *1 184CH₃ H H CH₃ H H *1 185 CH₃ H H CH₃ H H *1 186 CH₃ H H CH₃ H H *1 187 CH₃H H CH₃ H H *1 188 CH₃ H H CH₃ H H *1 189 CH₃ H H CH₃ H H *1 190 CH₃ H HCH₃ H H *1 191 CH₃ H H CH₃ H H *1 192 CH₃ H H CH₃ H H *1 193 CH₃ H H CH₃H H *1 194 CH₃ H H CH₃ H H *1 195 CH₃ H H CH₃ H H *1 196 CH₃ H H CH₃ H H*1 197 CH₃ H H CH₃ H H *1 198 CH₃ H H CH₃ H H *1 199 CH₃ H H CH₃ H H *1200 CH₃ H H CH₃ H H *1 201 CH₃ H H CH₃ H H *1 202 CH₃ H H CH₃ H H *1 203CH₃ H H CH₃ H H *1 204 CH₃ H H CH₃ H H *1 205 CH₃ H H CH₃ H H *1 206 CH₃H H CH₃ H H *1 207 CH₃ H H CH₃ H H *1 208 CH₃ H H CH₃ H H *1 209 CH₃ H HCH₃ H H *1 210 CH₃ H H CH₃ H H *1 211 CH₃ H H CH₃ H H *1 212 CH₃ H H CH₃H H *1 213 H H H H H H *1 214 CH₃ H H CH₃ H H *1 215 tert-C₄H₉ H Htert-C₄H₉ H H *1 216 Phenyl H H Phenyl H H *1 217 CH₃ H H CH₃ H H *1 218tert-C₄H₉ H H tert-C₄H₉ H H *1 219 H H H H H H *1 220 Phenyl H H PhenylH H *1 221 CH₃ H H CH₃ H H *1 222 tert-C₄H₉ H H tert-C₄H₉ H H *1 223Phenyl H H Phenyl H H *1 224 H H H H H H *1 225 tert-C₄H₉ H H tert-C₄H₉H H *1 226 tert-C₄H₉ H H tert-C₄H₉ H H *1 227 H H H H H H *1 228 CH₃ H HCH₃ H H *1 229 tert-C₄H₉ H H tert-C₄H₉ H H *1 230 Phenyl H H Phenyl H H*1

TABLE 3 Com- pound General formula (11) General formula (2a) Generalformula (2b) No. A^(x1) R^(x11) R^(x12) R^(x13) R^(x14) R^(a1) R^(a2)R^(a3) R^(a4) R^(a5) R^(a6) R^(a7) R^(a8) R^(a9) R^(b1) R^(b2) R^(b3)R^(b4) R^(b5) R^(b6) R^(b7) R^(b8) R^(b9) 231 CN General formula (2a)General formula (2a) General formula (2b) General formula (2b) H H H H HH H H *1 H H CH₃ H H CH₃ H H *1 232 CN General formula (2a) Generalformula (2a) General formula (2b) General formula (2b) H H H H H H H H*1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 233 CN General formula (2a)General formula (2a) General formula (2b) General formula (2b) H H H H HH H H *1 H H Phenyl H H Phenyl H H *1 234 CN General formula (2a)General formula (2a) General formula (2b) General formula (2b) H H H H HH H H *1 H H CH₃ H H H *1 235 CN General formula (2a) General formula(2a) General formula (2b) General formula (2b) H H H H H H H H *1 H Htert-C₄H₉ H H H H H *1 236 CN General formula (2a) General formula (2a)General formula (2b) General formula (2b) H H H H H H H H *1 H H PhenylH H H H H *1 237 CN General formula (2a) General formula (2a) Generalformula (2b) General formula (2b) H H H H H H H H *1 H H 9-Carbazolyl HH 9-Carbazolyl H H *1 238 CN General formula (2a) General formula (2a)General formula (2b) General formula (2b) H H H H H H H H *1 H Hiso-Butyl H H iso-Butyl H H *1 239 CN General formula (2a) Generalformula (2a) General formula (2b) General formula (2b) H H H H H H H H*1 H H 2-Ethylhexyl H H 2-Ethylhexyl H H *1 240 CN General formula (2a)General formula (2a) General formula (2b) General formula (2b) H H H H HH H H *1 H H Trimehylsilyl H H Trimehylsilyl H H *1 241 CN Generalformula (2a) General formula (2a) General formula (2b) General formula(2b) H H H H H H H H *1 H H Dipheylamino H H Dipheylamino H H *1 242 CNGeneral formula (2a) General formula (2a) General formula (2b) Generalformula (2b) H H H H H H H H *1 H H Dipheylamino H H H H H *1 243 CNGeneral formula (2a) General formula (2b) General formula (2a) Generalformula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 244 CN Generalformula (2a) General formula (2b) General formula (2a) General formula(2b) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 245 CNGeneral formula (2a) General formula (2b) General formula (2a) Generalformula (2b) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1 246 CNGeneral formula (2a) General formula (2b) General formula (2a) Generalformula (2b) H H H H H H H H *1 H H CH₃ H H H *1 247 CN General formula(2a) General formula (2b) General formula (2a) General formula (2b) H HH H H H H H *1 H H tert-C₄H₉ H H H H H *1 248 CN General formula (2a)General formula (2b) General formula (2a) General formula (2b) H H H H HH H H *1 H H Phenyl H H H H H *1 249 CN General formula (2a) Generalformula (2b) General formula (2a) General formula (2b) H H H H H H H H*1 H H 9-Carbazolyl H H 9-Carbazolyl H H *1 250 CN General formula (2a)General formula (2b) General formula (2a) General formula (2b) H H H H HH H H *1 H H iso-Butyl H H iso-Butyl H H *1 251 CN General formula (2a)General formula (2b) General formula (2a) General formula (2b) H H H H HH H H *1 H H 2-Ethylhexyl H H 2-Ethylhexyl H H *1 252 CN General formula(2a) General formula (2b) General formula (2a) General formula (2b) H HH H H H H H *1 H H Trimehylsilyl H H Trimehylsilyl H H *1 253 CN Generalformula (2a) General formula (2b) General formula (2a) General formula(2b) H H H H H H H H *1 H H Dipheylamino H H Dipheylamino H H *1 254 CNGeneral formula (2a) General formula (2b) General formula (2a) Generalformula (2b) H H H H H H H H *1 H H Dipheylamino H H H H H *1 255 CNGeneral formula (2a) General formula (2b) General formula (2b) Generalformula (2a) H H H H H H H H *1 H H CH₃ CH₃ H H *1 256 CN Generalformula (2a) General formula (2b) General formula (2b) General formula(2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 257 CNGeneral formula (2a) General formula (2b) General formula (2b) Generalformula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1 258 CNGeneral formula (2a) General formula (2b) General formula (2b) Generalformula (2a) H H H H H H H H *1 H H CH₃ H H H *1 259 CN General formula(2a) General formula (2b) General formula (2b) General formula (2a) H HH H H H H H *1 H H tert-C₄H₉ H H H H H *1 260 CN General formula (2a)General formula (2b) General formula (2b) General formula (2a) H H H H HH H H *1 H H Phenyl H H H H H *1 261 CN General formula (2a) Generalformula (2b) General formula (2b) General formula (2a) H H H H H H H H*1 H H 9-Carbazolyl H H 9-Carbazolyl H H *1 262 CN General formula (2a)General formula (2b) General formula (2b) General formula (2a) H H H H HH H H *1 H H iso-Butyl H H iso-Butyl H H *1 263 CN General formula (2a)General formula (2b) General formula (2b) General formula (2a) H H H H HH H H *1 H H 2-Ethylhexyl H H 2-Ethylhexyl H H *1 264 CN General formula(2a) General formula (2b) General formula (2b) General formula (2a) H HH H H H H H *1 H H Trimehylsilyl H H Trimehylsilyl H H *1 265 CN Generalformula (2a) General formula (2b) General formula (2b) General formula(2a) H H H H H H H H *1 H H Dipheylamino H H Dipheylamino H H *1 266 CNGeneral formula (2a) General formula (2b) General formula (2b) Generalformula (2a) H H H H H H H H *1 H H Dipheylamino H H H H H *1 267 CNGeneral formula (2a) General formula (2a) General formula (2b) Generalformula (2a) H H H H H H H H *1 H H CH₃ CH₃ H H *1 268 CN Generalformula (2a) General formula (2a) General formula (2b) General formula(2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 269 CNGeneral formula (2a) General formula (2a) General formula (2b) Generalformula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1 270 CNGeneral formula (2a) General formula (2a) General formula (2b) Generalformula (2a) H H H H H H H H *1 H H CH₃ H H H *1 271 CN General formula(2a) General formula (2a) General formula (2b) General formula (2a) H HH H H H H H *1 H H tert-C₄H₉ H H H H H *1 272 CN General formula (2a)General formula (2a) General formula (2b) General formula (2a) H H H H HH H H *1 H H Phenyl H H H H H *1 273 CN General formula (2a) Generalformula (2a) General formula (2b) General formula (2a) H H H H H H H H*1 H H H H H H H H *1 274 CN General formula (2a) General formula (2a)General formula (2b) General formula (2a) H H H H H H H H *1 H H H H H HH H *1 275 CN General formula (2a) General formula (2a) General formula(2b) General formula (2a) H H H H H H H H *1 H H H H H H H H *1 276 CNGeneral formula (2a) General formula (2a) General formula (2b) Generalformula (2a) H H H H H H H H *1 H H H H H H H H *1 277 CN Generalformula (2a) General formula (2a) General formula (2b) General formula(2a) H H H H H H H H *1 H H H H H H H H *1 278 CN General formula (2a)General formula (2a) General formula (2b) General formula (2a) H H H H HH H H *1 H H H H H H H H *1

TABLE 4-1 Com- pound General formula (10) General formula (2a) Generalformula 2b No. A¹ R¹ R² R³ R⁴ R⁵ R^(a1) R^(a2) R^(a3) R^(a4) R^(a5)R^(a6) R^(a7) R^(a8) R^(a9) R^(b1) R^(b2) R^(b3) R^(b4) R^(b5) R^(b6)R^(b7) R^(b8) R^(b9) 279 A1 General General General General formula (2b)General formula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula(2a) formula (2b) formula (2a) 280 A1 General General General Generalformula (2b) General formula (2a) H H H H H H H H *1 H H tert-C₄H₉ H Htert-C₄H₉ H H *1 formula (2a) formula (2b) formula (2a) 281 A1 GeneralGeneral General General formula (2b) General formula (2a) H H H H H H HH *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula (2b) formula (2a)282 A1 General General General General formula (2b) General formula (2a)H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2a)formula (2a) 283 A1 General General General General formula (2b) Generalformula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2a) formula (2a) 284 A1 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H PhenylH H Phenyl H H *1 formula (2a) formula (2a) formula (2a) 285 A1 GeneralGeneral General General formula (2b) General formula (2a) H H H H H H HH *1 H H 9-Carbazolyl H H 9-Carbazolyl H H *1 formula (2a) formula (2b)formula (2a) 286 A2 General General General General formula (2b) Generalformula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) formula (2a) 287 A2 General General General General formula(2b) General formula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉H H *1 formula (2a) formula (2b) formula (2a) 288 A2 General GeneralGeneral General formula (2b) General formula (2a) H H H H H H H H *1 H HPhenyl H H Phenyl H H *1 formula (2a) formula (2b) formula (2a) 289 A2General General General General formula (2b) General formula (2a) H H HH H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2a) formula(2a) 290 A2 General General General General formula (2b) General formula(2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a)formula (2a) formula (2a) 291 A2 General General General General formula(2b) General formula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H*1 formula (2a) formula (2a) formula (2a) 292 A2 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H9-Carbazolyl H H 9-Carbazolyl H H *1 formula (2a) formula (2b) formula(2a) 293 A3 General General General General formula (2b) General formula(2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)formula (2a) 294 A3 General General General General formula (2b) Generalformula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2b) formula (2a) 295 A3 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H PhenylH H Phenyl H H *1 formula (2a) formula (2b) formula (2a) 296 A3 GeneralGeneral General General formula (2b) General formula (2a) H H H H H H HH *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2a) formula (2a) 297A3 General General General General formula (2b) General formula (2a) H HH H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2a) formula (2a) 298 A3 General General General General formula (2b)General formula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2a) formula (2a) 299 A3 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H9-Carbazolyl H H 9-Carbazolyl H H *1 formula (2a) formula (2b) formula(2a) 300 A4 General General General General formula (2b) General formula(2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)formula (2a) 301 A4 General General General General formula (2b) Generalformula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2b) formula (2a) 302 A4 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H PhenylH H Phenyl H H *1 formula (2a) formula (2b) formula (2a) 303 A4 GeneralGeneral General General formula (2b) General formula (2a) H H H H H H HH *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2a) formula (2a) 304A4 General General General General formula (2b) General formula (2a) H HH H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2a) formula (2a) 305 A4 General General General General formula (2b)General formula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2a) formula (2a) 306 A4 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H9-Carbazolyl H H 9-Carbazolyl H H *1 formula (2a) formula (2b) formula(2a) 307 A5 General General General General formula (2b) General formula(2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)formula (2a) 308 A5 General General General General formula (2b) Generalformula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2b) formula (2a) 309 A5 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H PhenylH H Phenyl H H *1 formula (2a) formula (2b) formula (2a) 310 A5 GeneralGeneral General General formula (2b) General formula (2a) H H H H H H HH *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2a) formula (2a) 311A5 General General General General formula (2b) General formula (2a) H HH H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2a) formula (2a) 312 A5 General General General General formula (2b)General formula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2a) formula (2a) 313 A5 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H9-Carbazolyl H H 9-Carbazolyl H H *1 formula (2a) formula (2b) formula(2a) 314 A6 General General General General formula (2b) General formula(2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)formula (2a) 315 A6 General General General General formula (2b) Generalformula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2b) formula (2a) 316 A6 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H PhenylH H Phenyl H H *1 formula (2a) formula (2b) formula (2a) 317 A6 GeneralGeneral General General formula (2b) General formula (2a) H H H H H H HH *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2a) formula (2a) 318A6 General General General General formula (2b) General formula (2a) H HH H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2a) formula (2a) 319 A6 General General General General formula (2b)General formula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2a) formula (2a) 320 A6 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H9-Carbazolyl H H 9-Carbazolyl H H *1 formula (2a) formula (2b) formula(2a) 321 A7 General General General General formula (2b) General formula(2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)formula (2a) 322 A7 General General General General formula (2b) Generalformula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2b) formula (2a) 323 A7 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H PhenylH H Phenyl H H *1 formula (2a) formula (2b) formula (2a) 324 A7 GeneralGeneral General General formula (2b) General formula (2a) H H H H H H HH *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2a) formula (2a) 325A7 General General General General formula (2b) General formula (2a) H HH H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2a) formula (2a) 326 A7 General General General General formula (2b)General formula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2a) formula (2a) 327 A7 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H9-Carbazolyl H H 9-Carbazolyl H H *1 formula (2a) formula (2b) formula(2a) 328 A7 General General H General formula (2b) General formula (2a)H H H H H H H H *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula(2b) 329 A8 General General General General formula (2b) General formula(2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)formula (2a) 330 A8 General General General General formula (2b) Generalformula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2b) formula (2a) 331 A8 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H PhenylH H Phenyl H H *1 formula (2a) formula (2b) formula (2a) 332 A8 GeneralGeneral General General formula (2b) General formula (2a) H H H H H H HH *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2a) formula (2a) 333A8 General General General General formula (2b) General formula (2a) H HH H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2a) formula (2a) 334 A8 General General General General formula (2b)General formula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2a) formula (2a) 335 A8 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H9-Carbazolyl H H 9-Carbazolyl H H *1 formula (2a) formula (2b) formula(2a) 336 A9 General General General General formula (2b) General formula(2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)formula (2a) 337 A9 General General General General formula (2b) Generalformula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2b) formula (2a) 338 A9 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H PhenylH H Phenyl H H *1 formula (2a) formula (2b) formula (2a) 339 A9 GeneralGeneral General General formula (2b) General formula (2a) H H H H H H HH *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2a) formula (2a) 340A9 General General General General formula (2b) General formula (2a) H HH H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2a) formula (2a) 341 A9 General General General General formula (2b)General formula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2a) formula (2a) 342 A9 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H9-Carbazolyl H H 9-Carbazolyl H H *1 formula (2a) formula (2b) formula(2a) 343 A10 General General General General formula (2b) Generalformula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) formula (2a) 344 A10 General General General Generalformula (2b) General formula (2a) H H H H H H H H *1 H H tert-C₄H₉ H Htert-C₄H₉ H H *1 formula (2a) formula (2b) formula (2a) 345 A10 GeneralGeneral General General formula (2b) General formula (2a) H H H H H H HH *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula (2b) formula (2a)346 A10 General General General General formula (2b) General formula(2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2a)formula (2a) 347 A10 General General General General formula (2b)General formula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H*1 formula (2a) formula (2a) formula (2a) 348 A10 General GeneralGeneral General formula (2b) General formula (2a) H H H H H H H H *1 H HPhenyl H H Phenyl H H *1 formula (2a) formula (2a) formula (2a) 349 A10General General General General formula (2b) General formula (2a) H H HH H H H H *1 H H 9-Carbazolyl H H 9-Carbazolyl H H *1 formula (2a)formula (2b) formula (2a) 350 A11 General General General Generalformula (2b) General formula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H*1 formula (2a) formula (2b) formula (2a) 351 A11 General GeneralGeneral General formula (2b) General formula (2a) H H H H H H H H *1 H Htert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula (2b) formula (2a)352 A11 General General General General formula (2b) General formula(2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1 formula (2a)formula (2b) formula (2a) 353 A11 General General General Generalformula (2b) General formula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H*1 formula (2a) formula (2a) formula (2a) 354 A11 General GeneralGeneral General formula (2b) General formula (2a) H H H H H H H H *1 H Htert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula (2a) formula (2a)355 A11 General General General General formula (2b) General formula(2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1 formula (2a)formula (2a) formula (2a) 356 A11 General General General Generalformula (2b) General formula (2a) H H H H H H H H *1 H H 9-Carbazolyl HH 9-Carbazolyl H H *1 formula (2a) formula (2b) formula (2a) 357 A12General General General General formula (2b) General formula (2a) H H HH H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b) formula(2a) 358 A12 General General General General formula (2b) Generalformula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2b) formula (2a) 359 A12 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H PhenylH H Phenyl H H *1 formula (2a) formula (2b) formula (2a) 360 A12 GeneralGeneral General General formula (2b) General formula (2a) H H H H H H HH *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2a) formula (2a) 361A12 General General General General formula (2b) General formula (2a) HH H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2a) formula (2a) 362 A12 General General General General formula (2b)General formula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2a) formula (2a) 363 A12 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H9-Carbazolyl H H 9-Carbazolyl H H *1 formula (2a) formula (2b) formula(2a) 364 A13 General General General General formula (2b) Generalformula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) formula (2a) 365 A13 General General General Generalformula (2b) General formula (2a) H H H H H H H H *1 H H tert-C₄H₉ H Htert-C₄H₉ H H *1 formula (2a) formula (2b) formula (2a) 366 A13 GeneralGeneral General General formula (2b) General formula (2a) H H H H H H HH *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula (2b) formula (2a)367 A13 General General General General formula (2b) General formula(2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2a)formula (2a) 368 A13 General General General General formula (2b)General formula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H*1 formula (2a) formula (2a) formula (2a) 369 A13 General (2a) GeneralGeneral General formula (2b) General formula (2a) H H H H H H H H *1 H HPhenyl H H Phenyl H H *1 formula formula (2a) formula (2a) 370 A13General General General General formula (2b) General formula (2a) H H HH H H H H *1 H H 9-Carbazolyl H H 9-Carbazolyl H H *1 formula (2a)formula (2b) formula (2a)

TABLE 5-1 Com- pound General formula (10) General formula (2a) Generalformula (2b) No. A¹ R¹ R² R³ R⁴ R⁵ R^(a1) R^(a2) R^(a3) R^(a4) R^(a5)R^(a6) R^(a7) R^(a8) R^(a9) R^(b1) R^(b2) R^(b3) R^(b4) R^(b5) R^(b6)R^(b7) R^(b8) R^(b9) 371 A5 General A5 General General General formula(2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2a)formula (2b) 372 A5 General A5 General General General formula (2b) H HH H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2a) formula (2b) 373 A5 General A5 General General General formula (2b)H H H H H H H H *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula(2a) formula (2b) 374 A5 General A5 General General General formula (2b)H H CH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula(2a) formula (2b) 375 A5 General A5 General General General formula (2b)H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)formula (2a) 376 A5 General A5 General General General formula (2b) H HH H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2b) formula (2a) 377 A5 General A5 General General General formula (2b)H H H H H H H H *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula(2b) formula (2a) 378 A5 General A5 General General General formula (2b)H H CH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula(2b) formula (2a) 379 A5 General A5 General General General formula (2b)H H CH₃ H H CH₃ H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)formula (2a) 380 A5 General A5 General General General formula (2b) H HPhenyl H H Phenyl H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a)formula (2b) formula (2a) 381 A5 General A5 General General Generalformula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1 formula(2a) formula (2b) formula (2b) 382 A5 General A5 General General Generalformula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1 formula(2a) formula (2b) formula (2b) 383 A5 General A5 General General Generalformula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) formula (2b) 384 A5 General A5 General General Generalformula (2a) H H CH₃ H H CH₃ H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2b) formula (2b) 385 A5 General A5 General HGeneral formula (2b) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2b) 386 A5 General A5 General H General formula(2b) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1 formula (2a)formula (2b) 387 A5 General A5 General H General formula (2b) H H H H HH H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b) 388 A5 GeneralA5 General H General formula (2b) H H CH₃ H H CH₃ H H *1 H H tert-C₄H₉ HH tert-C₄H₉ H H *1 formula (2a) formula (2b) 389 A5 General A5 General HGeneral formula (2b) H H tert-C₄H₉ H H tert-C₄H₉ H H *1 H H Phenyl H HPhenyl H H *1 formula (2a) formula (2b) 390 A5 General A5 General HGeneral formula (2b) H H Phenyl H H Phenyl H H *1 H H Phenyl H H PhenylH H *1 formula (2a) formula (2b) 391 A6 General A6 General GeneralGeneral formula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula(2a) formula (2a) formula (2b) 392 A6 General A6 General General Generalformula (2b) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2a) formula (2b) 393 A6 General A6 General GeneralGeneral formula (2b) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2a) formula (2b) 394 A6 General A6 General GeneralGeneral formula (2b) H H CH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2a) formula (2b) 395 A6 General A6 General GeneralGeneral formula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula(2a) formula (2b) formula (2a) 396 A6 General A6 General General Generalformula (2b) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2b) formula (2a) 397 A6 General A6 General GeneralGeneral formula (2b) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2b) formula (2a) 398 A6 General A6 General GeneralGeneral formula (2b) H H CH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2b) formula (2a) 399 A6 General A6 General GeneralGeneral formula (2b) H H CH₃ H H CH₃ H H *1 H H CH₃ H H CH₃ H H *1formula (2a) formula (2b) formula (2a) 400 A6 General A6 General GeneralGeneral formula (2b) H H Phenyl H H Phenyl H H *1 H H tert-C₄H₉ H Htert-C₄H₉ H H *1 formula (2a) formula (2b) formula (2a) 401 A6 GeneralA6 General General General formula (2a) H H H H H H H H *1 H H Phenyl HH Phenyl H H *1 formula (2a) formula (2b) formula (2b) 402 A6 General A6General General General formula (2a) H H H H H H H H *1 H H Phenyl H HPhenyl H H *1 formula (2a) formula (2b) formula (2b) 403 A6 General A6General General General formula (2a) H H H H H H H H *1 H H CH₃ H H CH₃H H *1 formula (2a) formula (2b) formula (2b) 404 A6 General A6 GeneralGeneral General formula (2a) H H CH₃ H H CH₃ H H *1 H H tert-C₄H₉ H Htert-C₄H₉ H H *1 formula (2a) formula (2b) formula (2b) 405 A6 GeneralA6 General H General formula (2b) H H H H H H H H *1 H H Phenyl H HPhenyl H H *1 formula (2a) formula (2b) 406 A6 General A6 General HGeneral formula (2b) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2b) 407 A6 General A6 General H General formula(2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)408 A6 General A6 General H General formula (2b) H H CH₃ H H CH₃ H H *1H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula (2b) 409 A6General A6 General H General formula (2b) H H tert-C₄H₉ H H tert-C₄H₉ HH *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula (2b) 410 A6General A6 General H General formula (2b) H H Phenyl H H Phenyl H H *1 HH Phenyl H H Phenyl H H *1 formula (2a) formula (2b) 411 A7 General A7General General General formula (2b) H H H H H H H H *1 H H CH₃ H H CH₃H H *1 formula (2a) formula (2a) formula (2b) 412 A7 General A7 GeneralGeneral General formula (2b) H H H H H H H H *1 H H tert-C₄H₉ H Htert-C₄H₉ H H *1 formula (2a) formula (2a) formula (2b) 413 A7 GeneralA7 General General General formula (2b) H H H H H H H H *1 H H Phenyl HH Phenyl H H *1 formula (2a) formula (2a) formula (2b) 414 A7 General A7General General General formula (2b) H H CH₃ H H CH₃ H H *1 H H Phenyl HH Phenyl H H *1 formula (2a) formula (2a) formula (2b) 415 A7 General A7General General General formula (2b) H H H H H H H H *1 H H CH₃ H H CH₃H H *1 formula (2a) formula (2b) formula (2a) 416 A7 General A7 GeneralGeneral General formula (2b) H H H H H H H H *1 H H tert-C₄H₉ H Htert-C₄H₉ H H *1 formula (2a) formula (2b) formula (2a) 417 A7 GeneralA7 General General General formula (2b) H H H H H H H H *1 H H Phenyl HH Phenyl H H *1 formula (2a) formula (2b) formula (2a) 418 A7 General A7General General General formula (2b) H H CH₃ H H CH₃ H H *1 H H Phenyl HH Phenyl H H *1 formula (2a) formula (2b) formula (2a) 419 A7 General A7General General General formula (2b) H H CH₃ H H CH₃ H H *1 H H CH₃ H HCH₃ H H *1 formula (2a) formula (2b) formula (2a) 420 A7 General A7General General General formula (2b) H H Phenyl H H Phenyl H H *1 H Htert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula (2b) formula (2a)421 A7 General A7 General General General formula (2a) H H H H H H H H*1 H H Phenyl H H Phenyl H H *1 formula (2a) formula (2b) formula (2b)422 A7 General A7 General General General formula (2a) H H H H H H H H*1 H H Phenyl H H Phenyl H H *1 formula (2a) formula (2b) formula (2b)423 A7 General A7 General General General formula (2a) H H H H H H H H*1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b) formula (2b) 424 A7General A7 General General General formula (2a) H H CH₃ H H CH₃ H H *1 HH tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula (2b) formula (2b)425 A7 General A7 General H General formula (2b) H H H H H H H H *1 H HPhenyl H H Phenyl H H *1 formula (2a) formula (2b) 426 A7 General A7General H General formula (2b) H H H H H H H H *1 H H Phenyl H H PhenylH H *1 formula (2a) formula (2b) 427 A7 General A7 General H Generalformula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) 428 A7 General A7 General H General formula (2b) H H CH₃ HH CH₃ H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2b) 429 A7 General A7 General H General formula (2b) H H tert-C₄H₉ H Htert-C₄H₉ H H *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula (2b)430 A7 General A7 General H General formula (2b) H H Phenyl H H Phenyl HH *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula (2b) 431 A5General General A5 General General formula (2b) H H H H H H H H *1 H HCH₃ H H CH₃ H H *1 formula (2a) formula (2a) formula (2b) 432 A5 GeneralGeneral A5 General General formula (2b) H H H H H H H H *1 H H tert-C₄H₉H H tert-C₄H₉ H H *1 formula (2a) formula (2a) formula (2b) 433 A5General General A5 General General formula (2b) H H H H H H H H *1 H HPhenyl H H Phenyl H H *1 formula (2a) formula (2a) formula (2b) 434 A5General General A5 General General formula (2b) H H CH₃ H H CH₃ H H *1 HH Phenyl H H Phenyl H H *1 formula (2a) formula (2a) formula (2b) 435 A5General General A5 General General formula (2b) H H H H H H H H *1 H HCH₃ H H CH₃ H H *1 formula (2a) formula (2b) formula (2a) 436 A5 GeneralGeneral A5 General General formula (2b) H H H H H H H H *1 H H tert-C₄H₉H H tert-C₄H₉ H H *1 formula (2a) formula (2b) formula (2a) 437 A5General General A5 General General formula (2b) H H H H H H H H *1 H HPhenyl H H Phenyl H H *1 formula (2a) formula (2b) formula (2a) 438 A5General General A5 General General formula (2b) H H CH₃ H H CH₃ H H *1 HH Phenyl H H Phenyl H H *1 formula (2a) formula (2b) formula (2a) 439 A5General General A5 General General formula (2a) H H H H H H H H *1 H HCH₃ H H CH₃ H H *1 formula (2a) formula (2b) formula (2b) 440 A5 GeneralGeneral A5 General General formula (2a) H H H H H H H H *1 H H tert-C₄H₉H H tert-C₄H₉ H H *1 formula (2a) formula (2b) formula (2b) 441 A5General General A5 General General formula (2a) H H H H H H H H *1 H HPhenyl H H Phenyl H H *1 formula (2a) formula (2b) formula (2b) 442 A5General General A5 General General formula (2a) H H CH₃ H H CH₃ H H *1 HH Phenyl H H Phenyl H H *1 formula (2a) formula (2b) formula (2b) 443 A5General A5 General A5 General formula (2a) H H H H H H H H *1 H H CH₃ HH CH₃ H H *1 formula (2a) formula (2b) 444 A5 General A5 General A5General formula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H*1 formula (2a) formula (2b) 445 A5 General A5 General A5 Generalformula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1 formula(2a) formula (2b) 446 A5 General A5 General A5 General formula (2a) H HCH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula(2b) 447 A5 General A5 General A5 General formula (2a) H H H H H H H H*1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b) 448 A5 General A5General A5 General formula (2a) H H H H H H H H *1 H H tert-C₄H₉ H Htert-C₄H₉ H H *1 formula (2a) formula (2b) 449 A5 General A5 General A5General formula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2b) 450 A5 General A5 General A5 General formula(2a) H H CH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1 formula (2a)formula (2b) 451 A5 General A5 General A5 General formula (2a) H H H H HH H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b) 452 A5 GeneralA5 General A5 General formula (2a) H H H H H H H H *1 H H tert-C₄H₉ H Htert-C₄H₉ H H *1 formula (2a) formula (2b) 453 A5 General A5 General A5General formula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2b) 454 A5 General A5 General A5 General formula(2a) H H CH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1 formula (2a)formula (2b) 455 A6 General General A6 General General formula (2b) H HH H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2a) formula(2b) 456 A6 General General A6 General General formula (2b) H H H H H HH H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula (2a)formula (2b) 457 A6 General General A6 General General formula (2b) H HH H H H H H *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula (2a)formula (2b) 458 A6 General General A6 General General formula (2b) H HCH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula(2a) formula (2b) 459 A6 General General A6 General General formula (2b)H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)formula (2a) 460 A6 General General A6 General General formula (2b) H HH H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2b) formula (2a) 461 A6 General General A6 General General formula (2b)H H H H H H H H *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula(2b) formula (2a) 462 A6 General General A6 General General formula (2b)H H CH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula(2b) formula (2a) 463 A6 General General A6 General General formula (2a)H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)formula (2b) 464 A6 General General A6 General General formula (2a) H HH H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2b) formula (2b) 465 A6 General General A6 General General formula (2a)H H H H H H H H *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula(2b) formula (2b) 466 A6 General General A6 General General formula (2a)H H CH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula(2b) formula (2b) 467 A6 General A6 General A6 General formula (2a) H HH H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b) 468 A6General A6 General A6 General formula (2a) H H H H H H H H *1 H Htert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula (2b) 469 A6 GeneralA6 General A6 General formula (2a) H H H H H H H H *1 H H Phenyl H HPhenyl H H *1 formula (2a) formula (2b) 470 A6 General A6 General A6General formula (2a) H H CH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2b) 471 A6 General A6 General A6 General formula(2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)472 A6 General A6 General A6 General formula (2a) H H H H H H H H *1 H Htert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula (2b) 473 A6 GeneralA6 General A6 General formula (2a) H H H H H H H H *1 H H Phenyl H HPhenyl H H *1 formula (2a) formula (2b) 474 A6 General A6 General A6General formula (2a) H H CH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2b) 475 A6 General A6 General A6 General formula(2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)476 A6 General A6 General A6 General formula (2a) H H H H H H H H *1 H Htert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula (2b) 477 A6 GeneralA6 General A6 General formula (2a) H H H H H H H H *1 H H Phenyl H HPhenyl H H *1 formula (2a) formula (2b) 478 A6 General A6 General A6General formula (2a) H H CH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2b) 479 A7 General General A7 General Generalformula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2a) formula (2b) 480 A7 General General A7 General Generalformula (2b) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2a) formula (2b) 481 A7 General General A7 GeneralGeneral formula (2b) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2a) formula (2b) 482 A7 General General A7 GeneralGeneral formula (2b) H H CH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2a) formula (2b) 483 A7 General General A7 GeneralGeneral formula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula(2a) formula (2b) formula (2a) 484 A7 General General A7 General Generalformula (2b) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2b) formula (2a) 485 A7 General General A7 GeneralGeneral formula (2b) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2b) formula (2a) 486 A7 General General A7 GeneralGeneral formula (2b) H H CH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2b) formula (2a) 487 A7 General General A7 GeneralGeneral formula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula(2a) formula (2b) formula (2b) 488 A7 General General A7 General Generalformula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2b) formula (2b) 489 A7 General General A7 GeneralGeneral formula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2b) formula (2b) 490 A7 General General A7 GeneralGeneral formula (2a) H H CH₃ H H CH₃ H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2b) formula (2b) 491 A7 General A7 General A7General formula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula(2a) formula (2b) 492 A7 General A7 General A7 General formula (2a) H HH H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2b) 493 A7 General A7 General A7 General formula (2a) H H H H H H H H*1 H H Phenyl H H Phenyl H H *1 formula (2a) formula (2b) 494 A7 GeneralA7 General A7 General formula (2a) H H CH₃ H H CH₃ H H *1 H H Phenyl H HPhenyl H H *1 formula (2a) formula (2b) 495 A7 General A7 General A7General formula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula(2a) formula (2b) 496 A7 General A7 General A7 General formula (2a) H HH H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2b) 497 A7 General A7 General A7 General formula (2a) H H H H H H H H*1 H H Phenyl H H Phenyl H H *1 formula (2a) formula (2b) 498 A7 GeneralA7 General A7 General formula (2a) H H CH₃ H H CH₃ H H *1 H H Phenyl H HPhenyl H H *1 formula (2a) formula (2b) 499 A7 General A7 General A7General formula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula(2a) formula (2b) 500 A7 General A7 General A7 General formula (2a) H HH H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2b) 501 A7 General A7 General A7 General formula (2a) H H H H H H H H*1 H H Phenyl H H Phenyl H H *1 formula (2a) formula (2b) 502 A7 GeneralA7 General A7 General formula (2a) H H CH₃ H H CH₃ H H *1 H H Phenyl H HPhenyl H H *1 formula (2a) formula (2b)

TABLE 6-1 Com- pound General formula (10) General formula (2a) Generalformula (2b) No. A¹ R¹ R² R³ R⁴ R⁵ R^(a1) R^(a2) R^(a3) R^(a4) R^(a5)R^(a6) R^(a7) R^(a8) R^(a9) R^(b1) R^(b2) R^(b3) R^(b4) R^(b5) R^(b6)R^(b7) R^(b8) R^(b9) 503 CN General General A5 General formula (2b)General formula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula(2a) formula (2b) 504 CN General General A5 General formula (2a) Generalformula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) 505 CN General General A6 General formula (2b) Generalformula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) 506 CN General General A6 General formula (2a) Generalformula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) 507 CN General General A7 General formula (2b) Generalformula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) 508 CN General General A7 General formula (2a) Generalformula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) 509 CN General General A9 General formula (2b) Generalformula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) 510 CN General General A9 General formula (2a) Generalformula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) 511 CN General General A10 General formula (2b) Generalformula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) 512 CN General General A10 General formula (2a) Generalformula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) 513 A5 General General A5 General formula (2a) Generalformula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) 514 A5 General General A7 General formula (2b) Generalformula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) 515 A5 General General A9 General formula (2b) Generalformula (2a) H H CH₃ H H CH₃ H H *1 H H H H H H H H *1 formula (2a)formula (2b) 516 A5 General General A10 General formula (2b) Generalformula (2a) H H CH₃ H H CH₃ H H *1 H H H H H H H H *1 formula (2a)formula (2b) 517 A5 General General A10 General formula (2a) Generalformula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) 518 A7 General General H General formula (2b) Generalformula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a)formula (2b) 519 A7 General General H General formula (2b) Generalformula (2a) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2b) 520 A7 General General H General formula (2b)General formula (2a) H H H H H H H H *1 H H Phenyl H H Phenyl H H *1formula (2a) formula (2b) 521 A7 General General H General formula (2b)General formula (2a) H H CH₃ H H CH₃ H H *1 H H H H H H H H *1 formula(2a) formula (2b) 522 A7 General General H General formula (2b) Generalformula (2a) H H CH₃ H H CH₃ H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1formula (2a) formula (2b) 523 A7 General General H General formula (2b)General formula (2a) H H tert-C₄H₉ H H tert-C₄H₉ H H *1 H H H H H H H H*1 formula (2a) formula (2b) 524 A7 General General H General formula(2b) General formula (2a) H H tert-C₄H₉ H H tert-C₄H₉ H H *1 H H CH₃ H HCH₃ H H *1 formula (2a) formula (2b) 525 A7 General General H Generalformula (2b) General formula (2a) H H Phenyl H H Phenyl H H *1 H H H H HH H H *1 formula (2a) formula (2b) 526 A7 General General H Generalformula (2a) General formula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H*1 formula (2a) formula (2b) 527 A7 General General H General formula(2a) General formula (2b) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉H H *1 formula (2a) formula (2b) 528 A7 General General H Generalformula (2a) General formula (2b) H H tert-C₄H₉ H H tert-C₄H₉ H H *1 H HCH₃ H H CH₃ H H *1 formula (2a) formula (2b) 529 A7 General General A7General formula (2a) General formula (2b) H H H H H H H H *1 H H CH₃ H HCH₃ H H *1 formula (2a) formula (2b) 530 A7 General General A9 Generalformula (2b) General formula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H*1 formula (2a) formula (2b) 531 A7 General General A9 General formula(2b) General formula (2a) H H CH₃ H H CH₃ H H *1 H H H H H H H H *1formula (2a) formula (2b) 532 A7 General General A9 General formula (2a)General formula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula(2a) formula (2b) 533 A7 General General A10 General formula (2b)General formula (2a) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula(2a) formula (2b) 534 A7 General General A10 General formula (2b)General formula (2a) H H tert-C₄H₉ H H tert-C₄H₉ H H *1 H H H H H H H H*1 formula (2a) formula (2b) 535 A9 General General H General formula(2b) General formula (2a) H H tert-C₄H₉ H H tert-C₄H₉ H H *1 H H H H H HH H *1 formula (2a) formula (2b) 536 A9 General General H Generalformula (2b) General formula (2a) H H Phenyl H H Phenyl H H *1 H Htert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula (2b) 537 A9 GeneralGeneral H General formula (2b) General formula (2a) H H Phenyl H HPhenyl H H *1 H H H H H H H H *1 formula (2a) formula (2b) 538 A9General General H General formula (2b) General formula (2a) H H H H H HH H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b) 539 A9 GeneralGeneral H General formula (2b) General formula (2a) H H H H H H H H *1 HH H H H H H H *1 formula (2a) formula (2b) 540 A9 General General HGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H CH₃ H HCH₃ H H *1 formula (2a) formula (2b) 541 A9 General General H Generalformula (2a) General formula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H*1 formula (2a) formula (2b) 542 A9 General General H General formula(2a) General formula (2b) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉H H *1 formula (2a) formula (2b) 543 A9 General General H Generalformula (2a) General formula (2b) H H H H H H H H *1 H H Phenyl H HPhenyl H H *1 formula (2a) formula (2b) 544 A9 General General A9General formula (2b) General formula (2a) H H H H H H H H *1 H H CH₃ H HCH₃ H H *1 formula (2a) formula (2b) 545 A9 General General A9 Generalformula (2b) General formula (2a) H H H H H H H H *1 H H tert-C₄H₉ H Htert-C₄H₉ H H *1 formula (2a) formula (2b) 546 A9 General General A9General formula (2b) General formula (2a) H H H H H H H H *1 H H PhenylH H Phenyl H H *1 formula (2a) formula (2b) 547 A9 General General A9General formula (2b) General formula (2a) H H CH₃ H H CH₃ H H *1 H Htert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula (2b) 548 A9 GeneralGeneral A9 General formula (2a) General formula (2b) H H H H H H H H *1H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b) 549 A9 General GeneralA9 General formula (2a) General formula (2b) H H H H H H H H *1 H Htert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula (2b) 550 A9 GeneralGeneral A9 General formula (2a) General formula (2b) H H H H H H H H *1H H Phenyl H H Phenyl H H *1 formula (2a) formula (2b) 551 A9 GeneralGeneral A9 General formula (2a) General formula (2b) H H CH₃ H H CH₃ H H*1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula (2b) 552 A9General General A10 General formula (2b) General formula (2a) H H H H HH H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b) 553 A9 GeneralGeneral A10 General formula (2b) General formula (2a) H H H H H H H H *1H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula (2b) 554 A9General General A10 General formula (2b) General formula (2a) H H H H HH H H *1 H H Phenyl H H Phenyl H H *1 formula (2a) formula (2b) 555 A9General General A10 General formula (2b) General formula (2a) H H CH₃ HH CH₃ H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2b) 556 A9 General General A10 General formula (2b) General formula(2a) H H tert-C₄H₉ H H tert-C₄H₉ H H *1 H H H H H H H H *1 formula (2a)formula (2b) 557 A9 General General A10 General formula (2b) Generalformula (2a) H H tert-C₄H₉ H H tert-C₄H₉ H H *1 H H CH₃ H H CH₃ H H *1formula (2a) formula (2b) 558 A9 General General A10 General formula(2a) General formula (2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1formula (2a) formula (2b) 559 A9 General General A10 General formula(2a) General formula (2b) H H H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉H H *1 formula (2a) formula (2b) 560 A9 General General A10 Generalformula (2a) General formula (2b) H H H H H H H H *1 H H Phenyl H HPhenyl H H *1 formula (2a) formula (2b) 561 A9 General General A10General formula (2a) General formula (2b) H H CH₃ H H CH₃ H H *1 H H H HH H H H *1 formula (2a) formula (2b) 562 A10 General General GeneralGeneral formula (2b) General formula (2a) H H H H H H H H *1 H H CH₃ H HCH₃ H H *1 formula (2a) formula (2b) formula (2b) 563 A10 GeneralGeneral General General formula (2b) General formula (2a) H H CH₃ H HCH₃ H H *1 H H H H H H H H *1 formula (2a) formula (2b) formula (2b) 564A10 General General H General formula (2a) General formula (2b) H H H HH H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b) 565 A10General General A10 General formula (2b) General formula (2a) H H H H HH H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b) 566 A10General General A10 General formula (2b) General formula (2a) H H CH₃ HH CH₃ H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2b) 567 A10 General General A10 General formula (2a) General formula(2b) H H H H H H H H *1 H H CH₃ H H CH₃ H H *1 formula (2a) formula (2b)568 A10 General General A10 General formula (2a) General formula (2b) HH H H H H H H *1 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 formula (2a) formula(2b)

TABLE 7 Compound General formula (10) General formula (2a) No. A¹ R¹ R²R³ R⁴ R⁵ R^(a1) R^(a2) R^(a3) R^(a4) R^(a5) R^(a6) R^(a7) R^(a8) R^(a9)569 A5 General formula (2a) D11 H D11 General formula (2a) H H tert-C₄H₉H H tert-C₄H₉ H H *1 570 A5 D11 General formula (2a) H General formula(2a) D11 H H CH₃ H H CH₃ H H *1 571 A5 D24 General formula (2a) HGeneral formula (2a) D24 H H H H H H H H *1 572 A5 D24 General formula(2a) H General formula (2a) D24 H H CH₃ H H CH₃ H H *1 573 A5 D11General formula (2a) General formula (2a) General formula (2a) D11 H H HH H H H H *1 574 A5 D24 General formula (2a) General formula (2a)General formula (2a) D24 H H H H H H H H *1 575 A5 D11 General formula(2a) A5 D11 General formula (2a) H H H H H H H H *1 576 A5 D11 Generalformula (2a) A5 D11 General formula (2a) H H CH₃ H H CH₃ H H *1 577 A5D11 General formula (2a) A7 General formula (2a) D11 H H CH₃ H H CH₃ H H*1 578 A5 D11 General formula (2a) A9 General formula (2a) D11 H H H H HH H H *1 579 A5 D11 General formula (2a) A9 D11 General formula (2a) H HCH₃ H H CH₃ H H *1 580 A5 D24 General formula (2a) A9 General formula(2a) D24 H H CH₃ H H CH₃ H H *1 581 A5 General formula (2a) D11 A10 D11General formula (2a) H H H H H H H H *1 582 A5 General formula (2a) D11A10 D11 General formula (2a) H H CH₃ H H CH₃ H H *1 583 A5 D24 Generalformula (2a) A10 General formula (2a) D24 H H H H H H H H *1 584 A7 D11General formula (2a) H General formula (2a) D11 H H CH₃ H H CH₃ H H *1585 A7 D11 General formula (2a) H D11 General formula (2a) H H H H H H HH *1 586 A7 D11 General formula (2a) H D11 General formula (2a) H H CH₃H H CH₃ H H *1 587 A7 D11 General formula (2a) H D11 General formula(2a) H H tert-C₄H₉ H H tert-C₄H₉ H H *1 588 A7 D24 General formula (2a)H General formula (2a) D24 H H H H H H H H *1 589 A7 D11 General formula(2a) General formula (2a) General formula (2a) D11 H H H H H H H H *1590 A7 D11 General formula (2a) General formula (2a) General formula(2a) D11 H H CH₃ H H CH₃ H H *1 591 A7 D24 General formula (2a) Generalformula (2a) General formula (2a) D24 H H H H H H H H *1 592 A7 D11General formula (2a) A7 General formula (2a) D11 H H H H H H H H *1 593A7 D11 General formula (2a) A7 General formula (2a) D11 H H CH₃ H H CH₃H H *1 594 A7 General formula (2a) D11 A9 D11 General formula (2a) H HCH₃ H H CH₃ H H *1 595 A7 General formula (2a) D24 A9 D24 Generalformula (2a) H H H H H H H H *1 596 A7 General formula (2a) D24 A9 D24General formula (2a) H H CH₃ H H CH₃ H H *1 597 A7 D11 General formula(2a) A9 General formula (2a) D11 H H H H H H H H *1 598 A7 D24 Generalformula (2a) A9 General formula (2a) D24 H H H H H H H H *1 599 A7 D24General formula (2a) A9 General formula (2a) D24 H H CH₃ H H CH₃ H H *1600 A7 General formula (2a) D11 A10 D11 General formula (2a) H H H H H HH H *1 601 A7 General formula (2a) D11 A10 D11 General formula (2a) H HCH₃ H H CH₃ H H *1 602 A7 D11 General formula (2a) A10 General formula(2a) D11 H H H H H H H H *1 603 A7 D11 General formula (2a) A10 Generalformula (2a) D11 H H CH₃ H H CH₃ H H *1 604 A7 D24 General formula (2a)A10 General formula (2a) D24 H H H H H H H H *1 605 A7 D24 Generalformula (2a) A10 D24 General formula (2a) H H H H H H H H *1 606 A7General formula (2a) D11 H D11 General formula (2a) H H H H H H H H *1607 A7 General formula (2a) D11 H D11 General formula (2a) H H CH₃ H HCH₃ H H *1 608 A7 General formula (2a) D11 H D11 General formula (2a) HH Phenyl H H Phenyl H H *1 609 A7 D11 General formula (2a) H Generalformula (2a) D11 H H H H H H H H *1 610 A7 D11 General formula (2a) HGeneral formula (2a) D11 H H tert-C₄H₉ H H tert-C₄H₉ H H *1 611 A9General formula (2a) D24 A9 D24 General formula (2a) H H H H H h H H *1612 A9 General formula (2a) D24 A9 D24 General formula (2a) H H CH₃ H HCH₃ H H *1 613 A9 General formula (2a) D24 A10 D24 General formula (2a)H H H H H H H H *1 614 A9 General formula (2a) D24 A10 D24 Generalformula (2a) H H CH₃ H H CH₃ H H *1 615 A10 D11 General formula (2a) A10General formula (2a) D11 H H CH₃ H H CH₃ H H *1

TABLE 8 Compound General formula (10) No. A¹ R¹ R² R³ R⁴ R⁵ 616 CN D11CN D24 D11 D24 617 CN D11 D24 A7 D11 D24 618 A5 D11 D24 A9 D11 D24 619A5 D24 D11 A9 D11 D24 620 A5 D11 D24 A10 D11 D24 621 A7 D11 D24 H D11D24 622 A7 D24 D11 H D11 D24 623 A7 D11 D24 A9 D11 D24 624 A7 D11 D24 A9D24 D11 625 A7 D11 D24 A10 D24 D11 626 A7 D11 D24 A10 D11 D24 627 A7 D24D11 D11 D11 D24

In the following, specific examples of compounds that are not includedin the general formula (1) but are employable as the second organiccompound in the present invention are shown below.

Structures of D1 to D60 and A1 to A13 in the above Tables 1 to 8 areshown below.

[Third Organic Compound]

The third organic compound is a light-emitting material having a smallerlowest excited singlet energy than the first organic compound and thesecond organic compound. The third organic compound receives energy fromthe first organic compound and the second organic compound that are inan excited singlet state and from the second organic compound that hasbecome in an excited singlet state through reverse intersystem crossingfrom an excited triplet state, and transits to a singlet excited state,and thereafter when returning back to a ground state, it emitsfluorescence. The light-emitting material to be used as the thirdorganic compound is not specifically limited so far as it can receiveenergy from the first organic compound and the second organic compoundto emit light, and the light emission from the material may befluorescence or delayed fluorescence or may also be phosphorescence. Inparticular, the light-emitting material to be used as the third organiccompound is preferably one capable of emitting fluorescence whenreturning back from a lowest excited singlet energy level to a groundstate energy level. Two or more different types of third organiccompounds can be used so far as they satisfy the relationship of theformula (A). For example, by combining two or more kinds of thirdorganic compounds that differ in the emission color, it is possible toemit light of a desired color.

The third organic compound usable herein include an anthracenederivative, a tetracene derivative, a naphthacene derivative, a pyrenederivative, a perylene derivative, a chrysene derivative, a rubrenederivative, a coumarin derivative, a pyran derivative, a stilbenederivative, a fluorene derivative, an anthryl derivative, a terphenylderivative, a terphenylene derivative, a fluoranthene derivative, anamine derivative, a quinacridone derivative, an oxadiazole derivative, amalononitrile derivative, a carbazole derivative, a julolidinederivative, a thiazole derivative, and a derivative having a metal (Al,Zn). The skeleton of these derivatives may have a substituent, or maynot have a substituent. In the derivatives, plural skeletons can becombined.

Preferred examples of compounds usable as the third organic compound areshown below,

-   anthracene-   tetracene-   5,6,11,12-tetraphenyltetracene-   2,8-di-tert-butyl-5,11-bis(4-(tert-butyl)phenyl)-6,12-diphenyltetracene-   perylene-   2,5,8,11-tetra-tert-butylperylene-   1,3,6,8-tetraphenylpyrene-   benzo[e]pyrene-   5,12-dihydroquinolino[2,3-b]acridine-7,14-dione-   5,12-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione-   5,12-di-tert-butyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione-   5,12-di-tert-butyl-1,3,8,10-tetramethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione-   3-(benzo[d]thiazol-2-yl)-7-(diethylamino)-2H-chromen-2-one-   3-(1H-benzo[d]imidazol-2-yl)-7-(diethylamino)-2H-chromen-2-one-   7-(diethylamino)-3-(1-methyl-1H-benzo[d]imidazol-2-yl)-2H-chromen-2-one-   10-(benzo[d]thiazol-2-yl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one-   10-(benzo[d]thiazol-2-yl)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one-   7-(dimethylamino)-4-(trifluoromethyl)-2H-chromen-2-one-   7-(diethylamino)-4-(trifluoromethyl)-2H-chromen-2-one    1,1,7,7-tetramethyl-9-(trifluoromethyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyri    do[3,2,1-ij]quinolin-11-one-   (E)-2-(2-(4-(dimethylamino)styryl)-6-methyl-4H-pyran-4-ylidene)malononitrile-   (E)-2-(2-methyl-6-(2-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)vinyl)-4H-pyran-4-ylidene)malononitrile-   (E)-2-(2-methyl-6-(2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)vinyl)-4H-pyran-4-ylidene)malononitrile-   (E)-2-(2-(tert-butyl)-6-(2-(1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)vinyl)-4H-pyran-4-ylidene)malononitrile-   (E)-2-(2-(tert-butyl)-6-(2-(2,6,6-trimethyl-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)vinyl)-4H-pyran-4-ylidene)malononitrile-   (E)-2-(2-(4-(dimethylamino)styryl)-1-ethylquinolin-4(1H)-ylidene)malononitrile-   (E)-2-(2-(2-(7-(4-(bis(4-methoxyphenyl)amino)phenyl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)vinyl)-1-ethylquinolin-4(1H)-ylidene)malononitrile-   4,4′-((1E,1′E)-1,4-phenylenebis(ethene-2,1-diyl))bis(N,N-diphenylaniline)-   4,4′-((1E,1′E)-1,4-phenylenebis(ethene-2,1-diyl))bis(N,N-di-p-tolylaniline)-   1,4-bis((E)-4-(9H-carbazol-9-yl)styryl)benzene-   4,4′-((1E,1′E)-[1,1′-biphenyl]-4,4′-diylbis(ethene-2,1-diyl))bis(N,N-diphenylaniline)-   4,4′-((1E,1′E)-[1,1′-biphenyl]-4,4′-diylbis(ethene-2,1-diyl))bis(N,N-di-p-tolylaniline)-   4,4′-((1E,1′E)-9,9′-spirobi[fluorene]-2,7-diylbis(ethene-2,1-diyl))bis(N,N-diphenylaniline)-   4,4′-bis((E)-4-(9H-carbazol-9-yl)styryl)-1,1′-biphenyl-   4,4′-((1E,1′E)-naphthalene-2,6-diylbis(ethene-2,1-diyl))bis(N,N-diphenylaniline)-   4,4′-((1E,1′E)-naphthalene-2,6-diylbis(ethene-2,1-diyl))bis(N,N-bis(4-hexylphenyl)aniline)-   1,4-bis((E)-2-(9-ethyl-9H-carbazol-3-yl)vinyl)benzene-   4,4′-bis((E)-2-(9-ethyl-9H-carbazol-3-yl)vinyl)-1,1′-biphenyl-   1,1,4,4-tetraphenylbuta-1,3-diene-   (E)-N,N-diphenyl-4-styrylaniline-   (E)-N,N-diphenyl-4-(4-(pyren-1-yl)styryl)aniline-   (E)-9,9-diethyl-N,N-diphenyl-7-(4-(9-phenyl-9H-fluoren-9-yl)styryl)-9H-fluoren-2-amine-   tris(quinolin-8-yloxy)aluminum-   bis(2-(benzo[d]oxazol-2-yl)phenoxy)zinc-   bis(2-(benzo[d]thiazol-2-yl)phenoxy)zinc-   bis(quinolin-8-yloxy)zinc-   N4,N4,N4″′,N4″′-tetraphenyl-[1,1′: 4′,1″:    4″,1″′-quaterphenyl]-4,4″′-diamine-   9,9,9′,9′,    9″,9″-hexamethyl-N7,N7″-diphenyl-N7,N7″-di-m-tolyl-9H,9′H,9″H-[2,2′:    7′,2″-terfluorene]-7,7″-diamine-   9,9,9′,9′,    9″,9″-hexamethyl-N7,N7″-di(naphthalen-2-yl)-N7,N7″-diphenyl-9H,9′H,9″H-[2,    2′: 7′,2″-terfluorene]-7,7″-diamine-   N9,N10-diphenyl-N9,N10-di-p-tolylanthracene-9,10-diamine-   N9,N10-diphenyl-N9,N10-di-m-tolylanthracene-9,10-diamine-   N9,N10-di(naphthalen-2-yl)-N9,N10-diphenylanthracene-9,10-diamine-   N9,N9,N10,N10-tetra-p-tolylanthracene-9,10-diamine-   N10,N10,N10′,N10′-tetraphenyl-[9,9′-bianthracene]-10,10′-di amine-   N10,N10,N10′,N10′-tetra-p-tolyl-[9,9′-bianthracene]-10,10′-diamine-   N10,N10′-bis(4-isopropylphenyl)-N10,N10′-di-p-tolyl-[9,9′-bianthracene]-10,10′-diamine-   N10,N10′-di(naphthalen-1-yl)-N10,N10′-diphenyl-[9,9′-bianthracene]-10,10′-diamine-   N,N-diphenyldibenzo[g,p]chrysen-2-amine-   N5,N5,N9,N9-tetraphenylspiro[benzo[c]fluorene-7,9′-fluorene]-5,9-diamine-   N5,N9-diphenyl-N5,N9-di-m-tolylspiro[benzo[c]fluorene-7,9′-fluorene]-5,9-diamine-   2,6-bis(diphenylamino)anthracene-9,10-dione-   9,9′-diphenyl-9H,9′H-3,3′-bicarbazole-   3-(10-(naphthalen-1-yl)anthracen-9-yl)-9-phenyl-9H-carbazole-   cyclopenta-1,3-diene-1,2,3,4-tetrayltetrabenzene-   cyclopenta-1,3-diene-1,2,3,4,5-pentaylpentabenzene-   15,15-difluoro-3,11-dimesityl-15H-14l4,15l4-[1,3,5,2]triazaborinino[1,6-a:3,4-a′]diquinoline-   10,10′-bis(3,5-bis(trifluoromethyl)phenyl)-9,9′-bianthracene-   9,10-bis(4-(benzo[d]thiazol-2-yl)phenyl)anthracene

Light-emitting materials described in the following patent publicationscan be used as the third organic compound in the present invention.

JP2018-078242, JP2016-208021, JP2016-183331, WO2016/133058,WO2016/136425, JP2018-507909, WO2016/131521, JP2018-503619,WO2016/102048, JP2017-053941, WO2016/006674, JP2016-088927,JP2017-529316, WO2016/017919, WO2015/182547, JP2017-514878,WO2015/169412, WO2015/146912, JP2017-513855, WO2015/158411,JP2015-173263, JP2016-108297, JP2016-540381, WO2015/071473,WO2015/050057, WO2015/033559, JP2015-203027, JP2015-204357,JP2015-199670, JP2015-177138, WO2014/141725, JP2015-174901,JP2015-176694, JP2015-176693, WO2014/132917, WO2014/129048,JP2015-109370, JP2015-088563, WO2014/057874, JP2014-214148,JP2014-177442, JP2014-165346, JP2013-189426, WO2013/114941,JP2013-144675, JP2014-073986, JP2015-233024, JP2015-233023,JP2015-216135, JP2014-017373, JP2014-003247, JP2014-001349,JP2013-173726, JP2013-234221, WO2012/144176, JP2012-219098,JP2013-207139, JP2012-212662, WO2012/115218, JP2013-171736,JP2013-171735, JP2012-188416, JP2013-107845, WO2012/046839,JP2012-176928, JP2012-067077, JP2013-014525, JP2012-254948,JP2012-238445, JP2011-238922, JP2012-224569, JP2012-227244,JP2011-241383, WO2011/096506, WO2012/085982, WO2011/077691,WO2011/077690, WO2011/077689, WO2011/074254, WO2011/074253,WO2011/068083, JP2011-109098, JP2011-105718, JP2013-510890,WO2011/060877, JP2012-046478, JP2013-510889, WO2011/060859,JP2012-087187, JP2011-079822, JP2012-044010, JP2012-036096,JP2013-500585, WO2011/011501, JP2013-500281, WO2011/012212,JP2012-531383, WO2011/000455, JP2012-530695, WO2010/147318,JP2011-006405, WO2010/137285, JP2012-528208, WO2010/136110,JP2011-222831, JP2011-195515, JP2011-168550, JP2012-518275,WO2010/093457, JP2011-151108, JP2011-132419, JP2012-515734,WO2010/083873, JP2012-515733, WO2010/083872, JP2010-168363,JP2012-512912, WO2010/071871, JP2010-163430, JP2012-509317,WO2010/058946, JP2010-209059, JP2011-063550, WO2010/032453,WO2010/032447, JP2011-060878, JP2012-501354, WO2010/027181,JP2010-083868, WO2010/018842, JP2011-037743, WO2010/013676,JP2011-530802, WO2010/015306, JP2011-011994, WO2009/154207,WO2009/142230, JP2011-519971, WO2009/139580, JP2009-299049,WO2009/133917, JP2009-280576, JP2009-280571, JP2010-241874,JP2010-232533, JP2009-298770, WO2009/116628, JP2009-292806,WO2009/102054, WO2009/102026, JP2009-209133, JP2009-218568,JP2009-173642, JP2010-143879, JP2011-506564, WO2009/080716,JP2009-167175, WO2009/066600, JP2010-111635, JP2010-090085,JP2009-076450, JP2010-537383, WO2009/025810, JP2010-030973,JP2009-152529, JP2009-152528, WO2009/008357, WO2009/008311,JP2009-010364, WO2008/143229, JP2008-308685, JP2008-308673,WO2008/136522, JP2009-196970, JP2008-266309, JP2008-258603,WO2008/111554, WO2008/111553, JP2009-203203, WO2008/105472,WO2008/105471, JP2008-244465, WO2008/108177, JP2009-188136,JP2008-214339, JP2009-161468, JP2009-161465, JP2008-179614,JP2010-511696, WO2008/069586, WO2008/062773, JP2008-169197,JP2008-133264, JP2008-133263, WO2008/047744, JP2008-106063,JP2008-106055, JP2008-106054, JP2008-110965, JP2008-106044,JP2008-095080, JP2008-081497, JP2009-049094, JP2009-040731,JP2009-040730, JP2009-545156, WO2008/013399, JP2009-029725,JP2010-241687, JP2009-013066, JP2008-290999, JP2008-214332,JP2008-280312, JP2008-273861, JP2008-081490, JP2009-534376,WO2007/123339, JP2009-535813, WO2007/130259, JP2008-263112,WO2007/116828, JP2009-502778, WO2007/105917, JP2009-529035,WO2007/102683, JP2008-214271, JP2009-531341, WO2007/110129,WO2007/099983, JP2008-208065, JP2008-208039, WO2007/105448,JP2007-314510, JP2007-308477, JP2009-524653, WO2007/086695,JP2007-221113, JP2008-162911, JP2008-156316, JP2008-159779,JP2009-518342, WO2007/065678, JP2009-518328, WO2007/065550,JP2007-162009, WO2007/052759, JP2008-115093, JP2007-145834,JP2007-176928, JP2007-119457, JP2007-091721, JP2008-050308,JP2007-091715, JP2009-512179, WO2007/039344, JP2009-504730,WO2007/021117, JP2007-056006, JP2008-521243, WO2007/004799,JP2007-329176, JP2006-332668, JP2007-297302, JP2007-291012,JP2008-539189, WO2006/114364, JP2007-277113, JP2007-269736,JP2007-039431, JP2007-230887, WO2006/085434, JP2007-045809,JP2007-055996, WO2006/070712, WO2006/070711, JP2007-112729,JP2007-051208, JP2007-036127, JP2007-015961, JP2007-015933,JP2008-505449, WO2006/028546, WO2005/121057, JP2006-008663,WO2005/115950, JP2006-310351, JP2006-306732, JP2006-282533,WO2005/091686, JP2006-248900, JP2006-245172, JP2006-245021,JP2007-524745, WO2005/080527, JP2006-210747, JP2006-199629,JP2006-199628, JP2006-199595, JP2006-176448, WO2005/061656,WO2005/054162, WO2005/042621, JP2006-100756, JP2007-512685,WO2005/048370, JP2007-511067, WO2005/042668, WO2005/121203,WO2005/100437, JP2007-510294, WO2005/042667, JP2005-126431,JP2007-507449, WO2005/033051, JP2007-505074, WO2005/026088,JP2005-097283, JP2005-320277, JP2005-289842, JP2005-235633,JP2004-210786, JP2005-126399, JP2005-108746, JP2005-068366,WO2004/018587, JP2005-538999, WO2004/013080, JP2005-053806,JP2005-041804, JP2004-063465, WO2004/018588, JP2005-015420,JP2004-356033, JP2003-338377, JP2004-244400, JP2004-256469,JP2004-256468, JP2004-265623, JP2004-231563, JP2004-224766,JP2004-115441, JP2004-075580, JP2003-059668, JP2004-067528,JP2004-059535, JP2004-043646, JP2003-104916, JP2003-051388,JP2003-055652, JP2002-359081, JP2003-261560, JP2003-249372,JP2003-249371, JP2003-206289, JP2003-197375, JP2003-187980,JP2003-187979, JP2003-168563, JP2003-168562, JP2003-123978,JP2002-179630, JP2003-012612, JP2002-343569, JP2002-332420,JP2002-334784, JP2002-319490, JP2002-317175, JP2002-313575,JP2002-313573, WO2001/072673, JP2002-280182, JP2001-307885,JP2002-234892, JP2002-080822, JP2002-047282, JP2002-237386,JP2002-226484, JP2002-170682, JP2002-164176, JP2002-164175,WO2001/021729, JP2002-012861, JP2002-003833, JP2001-338763,JP2001-329257, JP2001-294585, JP2001-284050, JP2001-081090,JP2001-217077, JP2001-072683, JP2001-196179, JP2001-131434,JP2001-076876, JP2001-076875, JP2001-052869, JP2000-344691,JP2000-311786, JPH11-312588, JP2000-260569, JPH11-242995, JP2000-133457,JP2000-034234, JP2000-026325, JP2000-026324, JPH11-012205, JPH10-330295,JPH11-273864, JPH11-130817, JPH11-176575, JPH11-176573, JPH10-189248,JPH10-189247, JPH11-097178, WO1998/008360, JPH11-040360, JPH10-340783,JPH10-330743, JPH10-294179, JPH10-294177, JPH10-088122, JPH10-060427,JPH08-283256, JPH09-053068, JPH08-012600, JPH07-278537, JPH08-157815,JPH08-048726, JPH08-012967, JPH07-188340, JPH07-138561, JPH07-126330,JPH07-101911, JPH07-026254, JPH06-330032, JPH06-219973, JPH06-009892,JPH05-178810, JPH05-222361, JPH05-263072.

Here, JP indicates a Japanese patent publication, WO indicates aninternational patent publication, and H indicates Heisei. All the patentpublications described in this paragraph are referred to herein as apart of the present description.

The molecular weight of the second organic compound and the thirdorganic compound is, for example, in the case where an organic layercontaining the compound is intended to be formed according to a vapordeposition method and used in devices, preferably 1500 or less, morepreferably 1200 or less, even more preferably 1000 or less, and furthermore preferably 800 or less. Irrespective of the molecular weightthereof, the second organic compound and the third organic compound maybe formed into a film according to a coating method. When a coatingmethod is employed, even a compound having a relatively large molecularweight can be formed into a film.

Applying the present invention, it is considered to use a compoundcontaining plural structures represented by the above-mentioned generalformula in the molecule as a light-emitting material for the secondorganic compound or the third organic compound.

For example, the general formula (1) is described as an example. It isconsidered that a polymerizable group is previously introduced into astructure represented by the general formula (1) and the polymerizablegroup is polymerized to give a polymer, and the polymer is used as thesecond organic compound. Specifically, a monomer containing apolymerizable functional group in any of L, A and D in the generalformula (1) is prepared, and this is homo-polymerized or copolymerizedwith any other monomer to give a polymer having a recurring unit, andthe polymer can be used as a light-emitting material. Alternatively,compounds each having a structure represented by the general formula (1)are coupled to give a dimer or a trimer, and it can be used as alight-emitting material.

Examples of the polymer having a recurring unit containing a structurerepresented by the general formula (1), which is for use for the secondorganic compound or the third organic compound, include polymerscontaining a structure represented by the following general formula (23)or (24).

General Formula (23) General Formula (24)

In the general formula (23) or (24), Q represents a group containing astructure represented by the above-mentioned general formula, and L¹ andL² each represent a linking group. The carbon number of the linkinggroup is preferably 0 to 20, more preferably 1 to 15, even morepreferably 2 to 10. Preferably, the linking group has a structurerepresented by —X¹¹-L¹¹-. Here, X¹¹ represents an oxygen atom or asulfur atom, and is preferably an oxygen atom. L¹¹ represents a linkinggroup, and is preferably a substituted or unsubstituted alkylene group,or a substituted or unsubstituted arylene group, more preferably asubstituted or unsubstituted alkylene group having 1 to 10 carbon atoms,or a substituted or unsubstituted phenylene group.

In the general formula (23) or (24), R²⁰¹, R²⁰², R²⁰³ and R²⁰⁴ eachindependently represent a substituent. Preferably, the substituent is asubstituted or unsubstituted alkyl group having 1 to 6 carbon atoms, asubstituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, ora halogen atom, more preferably an unsubstituted alkyl group having 1 to3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbonatoms, a fluorine atom, or a chlorine atom, and even more preferably anunsubstituted alkyl group having 1 to 3 carbon atoms, or anunsubstituted alkoxy group having 1 to 3 carbon atoms.

The linking group represented by L¹ and L² may bond to any of L, A and Din the structure of the general formula (1) constituting Q. Two or morelinking groups may bond to one Q to form a crosslinked structure or anetwork structure.

Specific examples of the structure of the recurring unit includestructures represented by the following general formulae (25) to (28).

The polymer having the recurring unit containing the structurerepresented by any of the general formulae (25) to (28) may besynthesized in such a manner that a hydroxyl group is introduced to anyof L, A and D in the structure represented by the general formula (1),and the hydroxyl group as a linker is reacted with the followingcompound to introduce a polymerizable group thereinto, followed bypolymerizing the polymerizable group.

The polymer containing the structure represented by the above-mentionedgeneral formula in the molecule may be a polymer containing only arecurring unit having the structure represented by the general formula,or a polymer further containing a recurring unit having anotherstructure. The recurring unit having the structure represented by thegeneral formula contained in the polymer may be only one kind or two ormore kinds. Examples of the recurring unit that does not have thestructure represented by the general formula include a recurring unitderived from a monomer that is used for ordinary copolymerization.Examples of the recurring unit include a recurring unit derived from amonomer having an ethylenic unsaturated bond, such as ethylene andstyrene.

[Content of Compound and Combination of Compounds]

The content of each organic compound contained in the light-emittinglayer is not specifically limited but is preferably such that thecontent of the second organic compound is smaller than the content ofthe first organic compound. With that, a higher light emissionefficiency can be attained. Specifically, in the case where a totalweigh of the first organic compound having a content of W1, the secondorganic compound having a content of W2 and a third organic compoundhaving a content of W3 is 100% by weight, preferably, the content W1 ofthe first organic compound is 15% by weight or more and 99.9% by weightor less, the content W2 of the second organic compound is preferably5.0% by weight or more and 50% by weight or less, and the content W3 ofthe third organic compound is preferably 0.5% by weight or more and 5.0%by weight or less.

In producing an organic electroluminescent device, the first organiccompound, the second organic compound and the third organic compound canbe used in one layer alone, or may be used in the other layers. Forexample, one or more of the first organic compound, the second organiccompound and the third organic compound may be used in theabove-mentioned injection layer, blocking layer, hole blocking layerelectron blocking layer, exciton blocking layer, hole transport layerand an electron transport layer. Film formation methods for formingthese layers are not specifically limited, and the layers may be formedaccording to any of a dry process or a wet process.

Specific examples of a combination of the second organic compound andthe third organic compound in producing an organic electroluminescentdevice are shown in the following Tables. The vertical lines indicatethe compounds 1 to 678 exemplified as the second organic compound, andthe horizontal lines indicates the compounds D1 to D25 exemplified asthe third organic compound. The combinations specified by the secondorganic compound of the horizontal line and the third organic compoundof the vertical line are sequentially numbered as No. 1 to No. 16950.

Preferably, the first organic compound, the second organic compound andthe third organic compound for use in the present invention do notcontain a metal atom, and are more preferably compounds composed ofatoms selected from a carbon atom, a hydrogen atom, a nitrogen atom, anoxygen atom, a sulfur atom, a silicon atom, and a halogen atom (fluorineatom, chlorine atom, bromine atom, iodine atom). For example, it ispossible to select compounds composed of atoms alone selected from thegroup consisting of a carbon atom, a hydrogen atom, a nitrogen atom anda halogen atom (fluorine atom, chlorine atom, bromine atom, iodineatom), or to select compounds composed of atoms alone selected from thegroup consisting of a carbon atom, a hydrogen atom and a nitrogen atom.

TABLE 9-1 Third organic compound D1 D2 D3 D4 D5 D6 D7 D8 D9 D10 D11 D12D13 D14 D15 D16 D17 D18 D19 D20 D21 D22 D23 D24 D25 Second 1 1 2 3 4 5 67 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 organic 2 26 27 2829 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50compound 3 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 7071 72 73 74 75 4 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 9394 95 96 97 98 99 100 5 101 102 103 104 105 106 107 108 109 110 111 112113 114 115 116 117 118 119 120 121 122 123 124 125 6 126 127 128 129130 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147148 149 150 7 151 152 153 154 155 156 157 158 159 160 161 162 163 164165 166 167 168 169 170 171 172 173 174 175 8 176 177 178 179 180 181182 183 184 185 186 187 188 189 190 191 192 193 194 195 196 197 198 199200 9 201 202 203 204 205 206 207 208 209 210 211 212 213 214 215 216217 218 219 220 221 222 223 224 225 10 226 227 228 229 230 231 232 233234 235 236 237 238 239 240 241 242 243 244 245 246 247 248 249 250 11251 252 253 254 255 256 257 258 259 260 261 262 263 264 265 266 267 268269 270 271 272 273 274 275 12 276 277 278 279 280 281 282 283 284 285286 287 288 289 290 291 292 293 294 295 296 297 298 299 300 13 301 302303 304 305 306 307 308 309 310 311 312 313 314 315 316 317 318 319 320321 322 323 324 325 14 326 327 328 329 330 331 332 333 334 335 336 337338 339 340 341 342 343 344 345 346 347 348 349 350 15 351 352 353 354355 356 357 358 359 360 361 362 363 364 365 366 367 368 369 370 371 372373 374 375 16 376 377 378 379 380 381 382 383 384 385 386 387 388 389390 391 392 393 394 395 396 397 398 399 400 17 401 402 403 404 405 406407 408 409 410 411 412 413 414 415 416 417 418 419 420 421 422 423 424425 18 426 427 428 429 430 431 432 433 434 435 436 437 438 439 440 441442 443 444 445 446 447 448 449 450 19 451 452 453 454 455 456 457 458459 460 461 462 463 464 465 466 467 468 469 470 471 472 473 474 475 20476 477 478 479 480 481 482 483 484 485 486 487 488 489 490 491 492 493494 495 496 497 498 499 500 21 501 502 503 504 505 506 507 508 509 510511 512 513 514 515 516 517 518 519 520 521 522 523 524 525 22 526 527528 529 530 531 532 533 534 535 536 537 538 539 540 541 542 543 544 545546 547 548 549 550 23 551 552 553 554 555 556 557 558 559 560 561 562563 564 565 566 567 568 569 570 571 572 573 574 575 24 576 577 578 579580 581 582 583 584 585 586 587 588 589 590 591 592 593 594 595 596 597598 599 600 25 601 602 603 604 605 606 607 608 609 610 611 612 613 614615 616 617 618 619 620 621 622 623 624 625 26 626 627 628 629 630 631632 633 634 635 636 637 638 639 640 641 642 643 644 645 646 647 648 649650 27 651 652 653 654 655 656 657 658 659 660 661 662 663 664 665 666667 668 669 670 671 672 673 674 675 28 676 677 678 679 680 681 682 683684 685 686 687 688 689 690 691 692 693 694 695 696 697 698 699 700 29701 702 703 704 705 706 707 708 709 710 711 712 713 714 715 716 717 718719 720 721 722 723 724 725 30 726 727 728 729 730 731 732 733 734 735736 737 738 739 740 741 742 743 744 745 746 747 748 749 750 31 751 752753 754 755 756 757 758 759 760 761 762 763 764 765 766 767 768 769 770771 772 773 774 775 32 776 777 778 779 780 781 782 783 784 785 786 787788 789 790 791 792 793 794 795 796 797 798 799 800 33 801 802 803 804805 806 807 808 809 810 811 812 813 814 815 816 817 818 819 820 821 822823 824 825 34 826 827 828 829 830 831 832 833 834 835 836 837 838 839840 841 842 843 844 845 846 847 848 849 850 35 851 852 853 854 855 856857 858 859 860 861 862 863 864 865 866 867 868 869 870 871 872 873 874875 36 876 877 878 879 880 881 882 883 884 885 886 887 888 889 890 891892 893 894 895 896 897 898 899 900 37 901 902 903 904 905 906 907 908909 910 911 912 913 914 915 916 917 918 919 920 921 922 923 924 925 38926 927 928 929 930 931 932 933 934 935 936 937 938 939 940 941 942 943944 945 946 947 948 949 950 39 951 952 953 954 955 956 957 958 959 960961 962 963 964 965 966 967 968 969 970 971 972 973 974 975 40 976 977978 979 980 981 982 983 984 985 986 987 988 989 990 991 992 993 994 995996 997 998 999 1000 41 1001 1002 1003 1004 1005 1006 1007 1008 10091010 1011 1012 1013 1014 1015 1016 1017 1018 1019 1020 1021 1022 10231024 1025 42 1026 1027 1028 1029 1030 1031 1032 1033 1034 1035 1036 10371038 1039 1040 1041 1042 1043 1044 1045 1046 1047 1048 1049 1050 43 10511052 1053 1054 1055 1056 1057 1058 1059 1060 1061 1062 1063 1064 10651066 1067 1068 1069 1070 1071 1072 1073 1074 1075 44 1076 1077 1078 10791080 1081 1082 1083 1084 1085 1086 1087 1088 1089 1090 1091 1092 10931094 1095 1096 1097 1098 1099 1100 45 1101 1102 1103 1104 1105 1106 11071108 1109 1110 1111 1112 1113 1114 1115 1116 1117 1118 1119 1120 11211122 1123 1124 1125 46 1126 1127 1128 1129 1130 1131 1132 1133 1134 11351136 1137 1138 1139 1140 1141 1142 1143 1144 1145 1146 1147 1148 11491150 47 1151 1152 1153 1154 1155 1156 1157 1158 1159 1160 1161 1162 11631164 1165 1166 1167 1168 1169 1170 1171 1172 1173 1174 1175 48 1176 11771178 1179 1180 1181 1182 1183 1184 1185 1186 1187 1188 1189 1190 11911192 1193 1194 1195 1196 1197 1198 1199 1200 49 1201 1202 1203 1204 12051206 1207 1208 1209 1210 1211 1212 1213 1214 1215 1216 1217 1218 12191220 1221 1222 1223 1224 1225 50 1226 1227 1228 1229 1230 1231 1232 12331234 1235 1236 1237 1238 1239 1240 1241 1242 1243 1244 1245 1246 12471248 1249 1250 51 1251 1252 1253 1254 1255 1256 1257 1258 1259 1260 12611262 1263 1264 1265 1266 1267 1268 1269 1270 1271 1272 1273 1274 1275 521276 1277 1278 1279 1280 1281 1282 1283 1284 1285 1286 1287 1288 12891290 1291 1292 1293 1294 1295 1296 1297 1298 1299 1300 53 1301 1302 13031304 1305 1306 1307 1308 1309 1310 1311 1312 1313 1314 1315 1316 13171318 1319 1320 1321 1322 1323 1324 1325 54 1326 1327 1328 1329 1330 13311332 1333 1334 1335 1336 1337 1338 1339 1340 1341 1342 1343 1344 13451346 1347 1348 1349 1350 55 1351 1352 1353 1354 1355 1356 1357 1358 13591360 1361 1362 1363 1364 1365 1366 1367 1368 1369 1370 1371 1372 13731374 1375 56 1376 1377 1378 1379 1380 1381 1382 1383 1384 1385 1386 13871388 1389 1390 1391 1392 1393 1394 1395 1396 1397 1398 1399 1400 57 14011402 1403 1404 1405 1406 1407 1408 1409 1410 1411 1412 1413 1414 14151416 1417 1418 1419 1420 1421 1422 1423 1424 1425 58 1426 1427 1428 14291430 1431 1432 1433 1434 1435 1436 1437 1438 1439 1440 1441 1442 14431444 1445 1446 1447 1448 1449 1450 59 1451 1452 1453 1454 1455 1456 14571458 1459 1460 1461 1462 1463 1464 1465 1466 1467 1468 1469 1470 14711472 1473 1474 1475 60 1476 1477 1478 1479 1480 1481 1482 1483 1484 14851486 1487 1488 1489 1490 1491 1492 1493 1494 1495 1496 1497 1498 14991500 61 1501 1502 1503 1504 1505 1506 1507 1508 1509 1510 1511 1512 15131514 1515 1516 1517 1518 1519 1520 1521 1522 1523 1524 1525 62 1526 15271528 1529 1530 1531 1532 1533 1534 1535 1536 1537 1538 1539 1540 15411542 1543 1544 1545 1546 1547 1548 1549 1550 63 1551 1552 1553 1554 15551556 1557 1558 1559 1560 1561 1562 1563 1564 1565 1566 1567 1568 15691570 1571 1572 1573 1574 1575 64 1576 1577 1578 1579 1580 1581 1582 15831584 1585 1586 1587 1588 1589 1590 1591 1592 1593 1594 1595 1596 15971598 1599 1600 65 1601 1602 1603 1604 1605 1606 1607 1608 1609 1610 16111612 1613 1614 1615 1616 1617 1618 1619 1620 1621 1622 1623 1624 1625 661626 1627 1628 1629 1630 1631 1632 1633 1634 1635 1636 1637 1638 16391640 1641 1642 1643 1644 1645 1646 1647 1648 1649 1650 67 1651 1652 16531654 1655 1656 1657 1658 1659 1660 1661 1662 1663 1664 1665 1666 16671668 1669 1670 1671 1672 1673 1674 1675 68 1676 1677 1678 1679 1680 16811682 1683 1684 1685 1686 1687 1688 1689 1690 1691 1692 1693 1694 16951696 1697 1698 1699 1700 69 1701 1702 1703 1704 1705 1706 1707 1708 17091710 1711 1712 1713 1714 1715 1716 1717 1718 1719 1720 1721 1722 17231724 1725 70 1726 1727 1728 1729 1730 1731 1732 1733 1734 1735 1736 17371738 1739 1740 1741 1742 1743 1744 1745 1746 1747 1748 1749 1750 71 17511752 1753 1754 1755 1756 1757 1758 1759 1760 1761 1762 1763 1764 17651766 1767 1768 1769 1770 1771 1772 1773 1774 1775 72 1776 1777 1778 17791780 1781 1782 1783 1784 1785 1786 1787 1788 1789 1790 1791 1792 17931794 1795 1796 1797 1798 1799 1800 73 1801 1802 1803 1804 1805 1806 18071808 1809 1810 1811 1812 1813 1814 1815 1816 1817 1818 1819 1820 18211822 1823 1824 1825 74 1826 1827 1828 1829 1830 1831 1832 1833 1834 18351836 1837 1838 1839 1840 1841 1842 1843 1844 1845 1846 1847 1848 18491850 75 1851 1852 1853 1854 1855 1856 1857 1858 1859 1860 1861 1862 18631864 1865 1866 1867 1868 1869 1870 1871 1872 1873 1874 1875 76 1876 18771878 1879 1880 1881 1882 1883 1884 1885 1886 1887 1888 1889 1890 18911892 1893 1894 1895 1896 1897 1898 1899 1900 77 1901 1902 1903 1904 19051906 1907 1908 1909 1910 1911 1912 1913 1914 1915 1916 1917 1918 19191920 1921 1922 1923 1924 1925 78 1926 1927 1928 1929 1930 1931 1932 19331934 1935 1936 1937 1938 1939 1940 1941 1942 1943 1944 1945 1946 19471948 1949 1950 79 1951 1952 1953 1954 1955 1956 1957 1958 1959 1960 19611962 1963 1964 1965 1966 1967 1968 1969 1970 1971 1972 1973 1974 1975 801976 1977 1978 1979 1980 1981 1982 1983 1984 1985 1986 1987 1988 19891990 1991 1992 1993 1994 1995 1996 1997 1998 1999 2000 81 2001 2002 20032004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 20172018 2019 2020 2021 2022 2023 2024 2025 82 2026 2027 2028 2029 2030 20312032 2033 2034 2035 2036 2037 2038 2039 2040 2041 2042 2043 2044 20452046 2047 2048 2049 2050 83 2051 2052 2053 2054 2055 2056 2057 2058 20592060 2061 2062 2063 2064 2065 2066 2067 2068 2069 2070 2071 2072 20732074 2075 84 2076 2077 2078 2079 2080 2081 2082 2083 2084 2085 2086 20872088 2089 2090 2091 2092 2093 2094 2095 2096 2097 2098 2099 2100 85 21012102 2103 2104 2105 2106 2107 2108 2109 2110 2111 2112 2113 2114 21152116 2117 2118 2119 2120 2121 2122 2123 2124 2125 86 2126 2127 2128 21292130 2131 2132 2133 2134 2135 2136 2137 2138 2139 2140 2141 2142 21432144 2145 2146 2147 2148 2149 2150 87 2151 2152 2153 2154 2155 2156 21572158 2159 2160 2161 2162 2163 2164 2165 2166 2167 2168 2169 2170 21712172 2173 2174 2175 88 2176 2177 2178 2179 2180 2181 2182 2183 2184 21852186 2187 2188 2189 2190 2191 2192 2193 2194 2195 2196 2197 2198 21992200 89 2201 2202 2203 2204 2205 2206 2207 2208 2209 2210 2211 2212 22132214 2215 2216 2217 2218 2219 2220 2221 2222 2223 2224 2225 90 2226 22272228 2229 2230 2231 2232 2233 2234 2235 2236 2237 2238 2239 2240 22412242 2243 2244 2245 2246 2247 2248 2249 2250 91 2251 2252 2253 2254 22552256 2257 2258 2259 2260 2261 2262 2263 2264 2265 2266 2267 2268 22692270 2271 2272 2273 2274 2275 92 2276 2277 2278 2279 2280 2281 2282 22832284 2285 2286 2287 2288 2289 2290 2291 2292 2293 2294 2295 2296 22972298 2299 2300 93 2301 2302 2303 2304 2305 2306 2307 2308 2309 2310 23112312 2313 2314 2315 2316 2317 2318 2319 2320 2321 2322 2323 2324 2325 942326 2327 2328 2329 2330 2331 2332 2333 2334 2335 2336 2337 2338 23392340 2341 2342 2343 2344 2345 2346 2347 2348 2349 2350 95 2351 2352 23532354 2355 2356 2357 2358 2359 2360 2361 2362 2363 2364 2365 2366 23672368 2369 2370 2371 2372 2373 2374 2375 96 2376 2377 2378 2379 2380 23812382 2383 2384 2385 2386 2387 2388 2389 2390 2391 2392 2393 2394 23952396 2397 2398 2399 2400 97 2401 2402 2403 2404 2405 2406 2407 2408 24092410 2411 2412 2413 2414 2415 2416 2417 2418 2419 2420 2421 2422 24232424 2425 98 2426 2427 2428 2429 2430 2431 2432 2433 2434 2435 2436 24372438 2439 2340 2341 2342 2343 2344 2345 2346 2347 2348 2349 2350 99 24512452 2453 2454 2455 2456 2457 2458 2459 2460 2461 2462 2463 2464 24652466 2467 2468 2469 2470 2471 2472 2473 2474 2475 100 2476 2477 24782479 2480 2481 2482 2483 2484 2485 2486 2487 2488 2489 2490 2491 24922493 2494 2495 2496 2497 2498 2499 2500 101 2501 2502 2503 2504 25052506 2507 2508 2509 2510 2511 2512 2513 2514 2515 2516 2517 2518 25192520 2521 2522 2523 2524 2525 102 2526 2527 2528 2529 2530 2531 25322533 2534 2535 2536 2537 2538 2539 2540 2541 2542 2543 2544 2545 25462547 2548 2549 2550 103 2551 2552 2553 2554 2555 2556 2557 2558 25592560 2561 2562 2563 2564 2565 2566 2567 2568 2569 2570 2571 2572 25732574 2575 104 2576 2577 2578 2579 2580 2581 2582 2583 2584 2585 25862587 2588 2589 2590 2591 2592 2593 2594 2595 2596 2597 2598 2599 2600105 2601 2602 2603 2604 2605 2606 2607 2608 2609 2610 2611 2612 26132614 2615 2616 2617 2618 2619 2620 2621 2622 2623 2624 2625 106 26262627 2628 2629 2630 2631 2632 2633 2634 2635 2636 2637 2638 2639 26402641 2642 2643 2644 2645 2646 2647 2648 2649 2650 107 2651 2652 26532654 2655 2656 2657 2658 2659 2660 2661 2662 2663 2664 2665 2666 26672668 2669 2670 2671 2672 2673 2674 2675 108 2676 2677 2678 2679 26802681 2682 2683 2684 2685 2686 2687 2688 2689 2690 2691 2692 2693 26942695 2696 2697 2698 2699 2700 109 2701 2702 2703 2704 2705 2706 27072708 2709 2710 2711 2712 2713 2714 2715 2716 2717 2718 2719 2720 27212722 2723 2724 2725 110 2726 2727 2728 2729 2730 2731 2732 2733 27342735 2736 2737 2738 2739 2740 2741 2742 2743 2744 2745 2746 2747 27482749 2750 111 2751 2752 2753 2754 2755 2756 2757 2758 2759 2760 27612762 2763 2764 2765 2766 2767 2768 2769 2770 2771 2772 2773 2774 2775112 2776 2777 2778 2779 2780 2781 2782 2783 2784 2785 2786 2787 27882789 2790 2791 2792 2793 2794 2795 2796 2797 2798 2799 2800 113 28012802 2803 2804 2805 2806 2807 2808 2809 2810 2811 2812 2813 2814 28152816 2817 2818 2819 2820 2821 2822 2823 2824 2825 114 2826 2827 28282829 2830 2831 2832 2833 2834 2835 2836 2837 2838 2839 2840 2841 28422843 2844 2845 2846 2847 2848 2849 2850 115 2851 2852 2853 2854 28552856 2857 2858 2859 2860 2861 2862 2863 2864 2865 2866 2867 2868 28692870 2871 2872 2873 2874 2875 116 2876 2877 2878 2879 2880 2881 28822883 2884 2885 2886 2887 2888 2889 2890 2891 2892 2893 2894 2895 28962897 2898 2899 2900 117 2901 2902 2903 2904 2905 2906 2907 2908 29092910 2911 2912 2913 2914 2915 2916 2917 2918 2919 2920 2921 2922 29232924 2925 118 2926 2927 2928 2929 2930 2931 2932 2933 2934 2935 29362937 2938 2939 2940 2941 2942 2943 2944 2945 2946 2947 2948 2949 2950119 2951 2952 2953 2954 2955 2956 2957 2958 2959 2960 2961 2962 29632964 2965 2966 2967 2968 2969 2970 2971 2972 2973 2974 2975 120 29762977 2978 2979 2980 2981 2982 2983 2984 2985 2986 2987 2988 2989 29902991 2992 2993 2994 2995 2996 2997 2998 2999 3000 121 3001 3002 30033004 3005 3006 3007 3008 3009 3010 3011 3012 3013 3014 3015 3016 30173018 3019 3020 3021 3022 3023 3024 3025 122 3026 3027 3028 3029 30303031 3032 3033 3034 3035 3036 3037 3038 3039 3040 3041 3042 3043 30443045 3046 3047 3048 3049 3050 123 3051 3052 3053 3054 3055 3056 30573058 3059 3060 3061 3062 3063 3064 3065 3066 3067 3068 3069 3070 30713072 3073 3074 3075 124 3076 3077 3078 3079 3080 3081 3082 3083 30843085 3086 3087 3088 3089 3090 3091 3092 3093 3094 3095 3096 3097 30983099 3100 125 3101 3102 3103 3104 3105 3106 3107 3108 3109 3110 31113112 3113 3114 3115 3116 3117 3118 3119 3120 3121 3122 3123 3124 3125126 3126 3127 3128 3129 3130 3131 3132 3133 3134 3135 3136 3137 31383139 3140 3141 3142 3143 3144 3145 3146 3147 3148 3149 3150 127 31513152 3153 3154 3155 3156 3157 3158 3159 3160 3161 3162 3163 3164 31653166 3167 3168 3169 3170 3171 3172 3173 3174 3175 128 3176 3177 31783179 3180 3181 3182 3183 3184 3185 3186 3187 3188 3189 3190 3191 31923193 3194 3195 3196 3197 3198 3199 3200 129 3201 3202 3203 3204 32053206 3207 3208 3209 3210 3211 3212 3213 3214 3215 3216 3217 3218 32193220 3221 3222 3223 3224 3225 130 3226 3227 3228 3229 3230 3231 32323233 3234 3235 3236 3237 3238 3239 3240 3241 3242 3243 3244 3245 32463247 3248 3249 3250 131 3251 3252 3253 3254 3255 3256 3257 3258 32593260 3261 3262 3263 3264 3265 3266 3267 3268 3269 3270 3271 3272 32733274 3275 132 3276 3277 3278 3279 3280 3281 3282 3283 3284 3285 32863287 3288 3289 3290 3291 3292 3293 3294 3295 3296 3297 3298 3299 3300133 3301 3302 3303 3304 3305 3306 3307 3308 3309 3310 3311 3312 33133314 3315 3316 3317 3318 3319 3320 3321 3322 3323 3324 3325 134 33263327 3328 3329 3330 3331 3332 3333 3334 3335 3336 3337 3338 3339 33403341 3342 3343 3344 3345 3346 3347 3348 3349 3350 135 3351 3352 33533354 3355 3356 3357 3358 3359 3360 3361 3362 3363 3364 3365 3366 33673368 3369 3370 3371 3372 3373 3374 3375 136 3376 3377 3378 3379 33803381 3382 3383 3384 3385 3386 3387 3388 3389 3390 3391 3392 3393 33943395 3396 3397 3398 3399 3400 137 3401 3402 3403 3404 3405 3406 34073408 3409 3410 3411 3412 3413 3414 3415 3416 3417 3418 3419 3420 34213422 3423 3424 3425 138 3426 3427 3428 3429 3430 3431 3432 3433 34343435 3436 3437 3438 3439 3440 3441 3442 3443 3444 3445 3446 3447 34483449 3450 139 3451 3452 3453 3454 3455 3456 3457 3458 3459 3460 34613462 3463 3464 3465 3466 3467 3468 3469 3470 3471 3472 3473 3474 3475140 3476 3477 3478 3479 3480 3481 3482 3483 3484 3485 3486 3487 34883489 3490 3491 3492 3493 3494 3495 3496 3497 3498 3499 3500 141 35013502 3503 3504 3505 3506 3507 3508 3509 3510 3511 3512 3513 3514 35153516 3517 3518 3519 3520 3521 3522 3523 3524 3525 142 3526 3527 35283529 3530 3531 3532 3533 3534 3535 3536 3537 3538 3539 3540 3541 35423543 3544 3545 3546 3547 3548 3549 3550 143 3551 3552 3553 3554 35553556 3557 3558 3559 3560 3561 3562 3563 3564 3565 3566 3567 3568 35693570 3571 3572 3573 3574 3575 144 3576 3577 3578 3579 3580 3581 35823583 3584 3585 3586 3587 3588 3589 3590 3591 3592 3593 3594 3595 35963597 3598 3599 3600 145 3601 3602 3603 3604 3605 3606 3607 3608 36093610 3611 3612 3613 3614 3615 3616 3617 3618 3619 3620 3621 3622 36233624 3625 146 3626 3627 3628 3629 3630 3631 3632 3633 3634 3635 36363637 3638 3639 3640 3641 3642 3643 3644 3645 3646 3647 3648 3649 3650147 3651 3652 3653 3654 3655 3656 3657 3658 3659 3660 3661 3662 36633664 3665 3666 3667 3668 3669 3670 3671 3672 3673 3674 3675 148 36763677 3678 3679 3680 3681 3682 3683 3684 3685 3686 3687 3688 3689 36903691 3692 3693 3694 3695 3696 3697 3698 3699 3700 149 3701 3702 37033704 3705 3706 3707 3708 3709 3710 3711 3712 3713 3714 3715 3716 37173718 3719 3720 3721 3722 3723 3724 3725 150 3726 3727 3728 3729 37303731 3732 3733 3734 3735 3736 3737 3738 3739 3740 3741 3742 3743 37443745 3746 3747 3748 3749 3750 151 3751 3752 3753 3754 3755 3756 37573758 3759 3760 3761 3762 3763 3764 3765 3766 3767 3768 3769 3770 37713772 3773 3774 3775 152 3776 3777 3778 3779 3780 3781 3782 3783 37843785 3786 3787 3788 3789 3790 3791 3792 3793 3794 3795 3796 3797 37983799 3800 153 3801 3802 3803 3804 3805 3806 3807 3808 3809 3810 38113812 3813 3814 3815 3816 3817 3818 3819 3820 3821 3822 3823 3824 3825154 3826 3827 3828 3829 3830 3831 3832 3833 3834 3835 3836 3837 38383839 3840 3841 3842 3843 3844 3845 3846 3847 3848 3849 3850 155 38513852 3853 3854 3855 3856 3857 3858 3859 3860 3861 3862 3863 3864 38653866 3867 3868 3869 3870 3871 3872 3873 3874 3875 156 3876 3877 38783879 3880 3881 3882 3883 3884 3885 3886 3887 3888 3889 3890 3891 38923893 3894 3895 3896 3897 3898 3899 3900 157 3901 3902 3903 3904 39053906 3907 3908 3909 3910 3911 3912 3913 3914 3915 3916 3917 3918 39193920 3921 3922 3923 3924 3925 158 3926 3927 3928 3929 3930 3931 39323933 3934 3935 3936 3937 3938 3939 3940 3941 3942 3943 3944 3945 39463947 3948 3949 3950 159 3951 3952 3953 3954 3955 3956 3957 3958 39593960 3961 3962 3963 3964 3965 3966 3967 3968 3969 3970 3971 3972 39733974 3975 160 3976 3977 3978 3979 3980 3981 3982 3983 3984 3985 39863987 3988 3989 3990 3991 3992 3993 3994 3995 3996 3997 3998 3999 4000161 4001 4002 4003 4004 4005 4006 4007 4008 4009 4010 4011 4012 40134014 4015 4016 4017 4018 4019 4020 4021 4022 4023 4024 4025 162 40264027 4028 4029 4030 4031 4032 4033 4034 4035 4036 4037 4038 4039 40404041 4042 4043 4044 4045 4046 4047 4048 4049 4050 163 4051 4052 40534054 4055 4056 4057 4058 4059 4060 4061 4062 4063 4064 4065 4066 40674068 4069 4070 4071 4072 4073 4074 4075 164 4076 4077 4078 4079 40804081 4082 4083 4084 4085 4086 4087 4088 4089 4090 4091 4092 4093 40944095 4096 4097 4098 4099 4100 165 4101 4102 4103 4104 4105 4106 41074108 4109 4110 4111 4112 4113 4114 4115 4116 4117 4118 4119 4120 41214122 4123 4124 4125 166 4126 4127 4128 4129 4130 4131 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[Other Organic Compounds]

The light-emitting layer may be composed of only the first organiccompound to the third organic compound, and may contain any otherorganic compound than the first organic compound to the third organiccompound. Examples of the other organic compound than the first organiccompound to the third organic compound include an organic compoundhaving hole transport competence, and an organic compound havingelectron transport competence. Regarding the organic compound havinghole transport competence, and the organic compound having electrontransport competence, reference may be made to the hole transportmaterial and the electron transport material mentioned hereinunder.

[Substrate]

The organic electroluminescent device of the invention is preferablysupported by a substrate. The substrate is not particularly limited andmay be those that have been commonly used in an organicelectroluminescent device, and examples thereof used include thoseformed of glass, transparent plastics, quartz and silicon.

[Anode]

The anode of the organic electroluminescent device used is preferablyformed of, as an electrode material, a metal, an alloy, or anelectroconductive compound each having a large work function (4 eV ormore), or a mixture thereof. Specific examples of the electrode materialinclude a metal, such as Au, and an electroconductive transparentmaterial, such as CuI, indium tin oxide (ITO), SnO₂ and ZnO. A materialthat is amorphous and is capable of forming a transparentelectroconductive film, such as IDIXO (In₂O₃—ZnO), may also be used. Theanode may be formed in such a manner that the electrode material isformed into a thin film by such a method as vapor deposition orsputtering, and the film is patterned into a desired pattern by aphotolithography method, or in the case where the pattern may notrequire high accuracy (for example, approximately 100 μm or more), thepattern may be formed with a mask having a desired shape on vapordeposition or sputtering of the electrode material. In alternative, inthe case where a material capable of being coated, such as an organicelectroconductive compound, is used, a wet film forming method, such asa printing method and a coating method, may be used. In the case whereemitted light is to be taken out through the anode, the anode preferablyhas a transmittance of more than 10%, and the anode preferably has asheet resistance of several hundred Ω/sq or less. The thickness of theanode may be generally selected from a range of from 10 to 1,000 nm, andpreferably from 10 to 200 nm, while depending on the material used.

[Cathode]

The cathode is preferably formed of, as an electrode material, a metal(which is referred to as an electron injection metal), an alloy, or anelectroconductive compound, having a small work function (4 eV or less),or a mixture thereof. Specific examples of the electrode materialinclude sodium, a sodium-potassium alloy, magnesium, lithium, amagnesium-cupper mixture, a magnesium-silver mixture, amagnesium-aluminum mixture, a magnesium-indium mixture, analuminum-aluminum oxide (Al₂O₃) mixture, indium, a lithium-aluminummixture, and a rare earth metal. Among these, a mixture of an electroninjection metal and a second metal that is a stable metal having alarger work function than the electron injection metal, for example, amagnesium-silver mixture, a magnesium-aluminum mixture, amagnesium-indium mixture, an aluminum-aluminum oxide (Al₂O₃) mixture, alithium-aluminum mixture, and aluminum, is preferred from the standpointof the electron injection property and the durability against oxidationand the like. The cathode may be produced by forming the electrodematerial into a thin film by such a method as vapor deposition orsputtering. The cathode preferably has a sheet resistance of severalhundred Q/sq or less, and the thickness thereof may be generallyselected from a range of from 10 nm to 5 μm, and preferably from 50 to200 nm. For transmitting the emitted light, any one of the anode and thecathode of the organic electroluminescent device is preferablytransparent or translucent, thereby enhancing the light emissionluminance.

The cathode may be formed with the electroconductive transparentmaterials described for the anode, thereby forming a transparent ortranslucent cathode, and by applying the cathode, a device having ananode and a cathode, both of which have transmittance, may be produced.

[Injection Layer]

The injection layer is a layer that is provided between the electrodeand the organic layer, for decreasing the driving voltage and enhancingthe light emission luminance, and includes a hole injection layer and anelectron injection layer, which may be provided between the anode andthe light-emitting layer or the hole transport layer and between thecathode and the light emitting layer or the electron transport layer.The injection layer may be provided depending on necessity.

[Blocking Layer]

The blocking layer is a layer that is capable of inhibiting charges(electrons or holes) and/or excitons present in the light-emitting layerfrom being diffused outside the light-emitting layer. The electronblocking layer may be disposed between the light-emitting layer and thehole transport layer, and inhibits electrons from passing through thelight-emitting layer toward the hole transport layer. Similarly, thehole blocking layer may be disposed between the light-emitting layer andthe electron transport layer, and inhibits holes from passing throughthe light-emitting layer toward the electron transport layer. Theblocking layer may also be used for inhibiting excitons from beingdiffused outside the light-emitting layer. Thus, the electron blockinglayer and the hole blocking layer each may also have a function as anexciton blocking layer. The term “the electron blocking layer” or “theexciton blocking layer” referred to herein is intended to include alayer that has both the functions of an electron blocking layer and anexciton blocking layer by one layer.

[Hole Blocking Layer]

The hole blocking layer has the function of an electron transport layerin a broad sense. The hole blocking layer has a role of inhibiting holesfrom reaching the electron transport layer while transporting electrons,and thereby enhances the recombination probability of electrons andholes in the light-emitting layer. As the material for the hole blockinglayer, the material for the electron transport layer to be mentionedbelow may be used optionally.

[Electron Blocking Layer]

The electron blocking layer has the function of transporting holes in abroad sense. The electron blocking layer has a role of inhibitingelectrons from reaching the hole transport layer while transportingholes, and thereby enhances the recombination probability of electronsand holes in the light-emitting layer.

[Exciton Blocking Layer]

The exciton blocking layer is a layer for inhibiting excitons generatedthrough recombination of holes and electrons in the light-emitting layerfrom being diffused to the charge transporting layer, and the use of thelayer inserted enables effective confinement of excitons in thelight-emitting layer, and thereby enhances the light emission efficiencyof the device. The exciton blocking layer may be adjacent to thelight-emitting layer to be inserted on any of the side of the anode andthe side of the cathode, and on both the sides. Specifically, in thecase where the exciton blocking layer is present on the side of theanode, the layer may be inserted between the hole transport layer andthe light-emitting layer and adjacent to the light-emitting layer, andin the case where the layer is inserted on the side of the cathode, thelayer may be inserted between the light-emitting layer and the cathodeand adjacent to the light-emitting layer. Between the anode and theexciton blocking layer that is adjacent to the light-emitting layer onthe side of the anode, a hole injection layer, an electron blockinglayer and the like may be provided, and between the cathode and theexciton blocking layer that is adjacent to the light-emitting layer onthe side of the cathode, an electron injection layer, an electrontransport layer, a hole blocking layer and the like may be provided. Inthe case where the blocking layer is provided, preferably, at least oneof the excited singlet energy and the excited triplet energy of thematerial used as the blocking layer is higher than the excited singletenergy and the excited triplet energy of the light-emitting layer of thelight-emitting material.

[Hole Transport Layer]

The hole transport layer is formed of a hole transport material having afunction of transporting holes, and the hole transport layer may beprovided as a single layer or plural layers.

The hole transport material has one of injection or transportingproperty of holes and blocking property of electrons, and may be any ofan organic material and an inorganic material. Examples of known holetransport materials that may be used herein include a triazolederivative, an oxadiazole derivative, an imidazole derivative, acarbazole derivative, an indolocarbazole derivative, a polyarylalkanederivative, a pyrazoline derivative, a pyrazolone derivative, aphenylenediamine derivative, an arylamine derivative, anamino-substituted chalcone derivative, an oxazole derivative, astyrylanthracene derivative, a fluorenone derivative, a hydrazonederivative, a stilbene derivative, a silazane derivative, an anilinecopolymer and an electroconductive polymer oligomer, particularly athiophene oligomer. A porphyrin compound, an aromatic tertiary aminecompound and a styrylamine compound are preferably used, and an aromatictertiary amine compound is more preferably used.

[Electron Transport Layer]

The electron transport layer is formed of a material having a functionof transporting electrons, and the electron transport layer may be asingle layer or may be formed of plural layers.

The electron transport material (often also acting as a hole blockingmaterial) may have a function of transmitting the electrons injectedfrom a cathode to a light-emitting layer. The electron transport layerusable here includes, for example, nitro-substituted fluorenederivatives, diphenylquinone derivatives, thiopyran dioxide derivatives,carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethaneand anthrone derivatives, oxadiazole derivatives, etc. Further,thiadiazole derivatives derived from the above-mentioned oxadiazolederivatives by substituting the oxygen atom in the oxadiazole ring witha sulfur atom, and quinoxaline derivatives having a quinoxaline ringknown as an electron-attractive group are also usable as the electrontransport material. Further, polymer materials prepared by introducingthese materials into the polymer chain, or having these material in thepolymer main chain are also usable.

[Exemplification of Materials Usable in Organic ElectroluminescentDevice]

Preferred materials for use for the organic electroluminescent deviceare concretely exemplified below. However, the materials for use in thepresent invention are not limitatively interpreted by the followingexemplary compounds. Compounds, even though exemplified as materialshaving a specific function, can also be used as other materials havingany other function. R, and R₂ to R₇ in the structural formulae of thefollowing exemplary compounds each independently represent a hydrogenatom or a substituent, n represents an integer of 3 to 5.

First, preferred compounds for use as a hole injection material arementioned below.

Next, preferred compounds for use as a hole transport material arementioned below.

Next, preferred compounds for use as an electron blocking material arementioned below.

Next, preferred compounds for use as a hole blocking material arementioned below.

Next, preferred compounds for use as an electron transport material arementioned below.

Next, preferred compounds for use as an electron injection material arementioned below.

Further, preferred compounds for use as additional materials arementioned below. For example, these are considered to be added as astabilization material.

[Light Emission]

The organic electroluminescent device thus produced by theaforementioned method emits light on application of an electric fieldbetween the anode and the cathode of the device. In this case, when thelight emission is caused by the excited singlet energy, light having awavelength that corresponds to the energy level thereof may be confirmedas fluorescent light and delayed fluorescent light. When the lightemission is caused by the excited triplet energy, light having awavelength that corresponds to the energy level thereof may be confirmedas phosphorescent light. The normal fluorescent light has a shorterlight emission lifetime than the delayed fluorescent light, and thus thelight emission lifetime may be distinguished between the fluorescentlight and the delayed fluorescent light.

On the other hand, the phosphorescent light may substantially not beobserved with an ordinary organic compound such as the compounds of thepresent invention at room temperature since the excited triplet energythereof is unstable and is converted into heat or the like, that is, thelifetime is short and the compound may immediately deactivate. Theexcited triplet energy of an ordinary organic compound may be measuredby observing light emission under an extremely low temperaturecondition.

[Application]

The organic electroluminescent device of the invention may be applied toany of a single device, a structure with plural devices disposed in anarray, and a structure having anodes and cathodes disposed in an X-Ymatrix. According to the present invention using the first organiccompound, the second organic compound and the third organic compoundsatisfying the requirement in the present invention, in a light-emittinglayer, an organic light-emitting device having a markedly improved lightemission efficiency can be obtained. The organic light-emitting devicesuch as the organic electroluminescent device of the present inventionmay be applied to a further wide range of purposes. For example, anorganic electroluminescent display apparatus may be produced with theorganic electroluminescent device of the invention, and for the detailsthereof, reference may be made to S. Tokito, C. Adachi and H. Murata,“Yuki EL Display” (Organic EL Display) (Ohmsha, Ltd.). In particular,the organic electroluminescent device of the invention may be applied toorganic electroluminescent illumination and backlight which are highlydemanded.

EXAMPLES

The features of the present invention will be described morespecifically with reference to Examples given below. The materials,processes, procedures and the like shown below may be appropriatelymodified unless they deviate from the substance of the invention.Accordingly, the scope of the invention is not construed as beinglimited to the specific examples shown below. The light emissioncharacteristics were evaluated using a high-performance UV-visiblelight-near IR spectrophotometer (available from Perkin Elmer, Lambda950), a fluorescence spectrophotometer (available from Horiba, Ltd.,FluoroMax-4), an absolute PL quantum yield meter (available fromHamamatsu Photonics K.K., C11347), a source meter (available fromKeithley Instruments Corporation: 2400 series), a semiconductorparameter analyzer (available from Agilent Technologies, E5273A), anoptical power meter device (available from Newport Corporation, 1930C),an optical spectroscope (available from Ocean Optics Corporation,USB2000), a spectroradiometer (available from Topcon Corporation, SR-3),and a streak camera (available from Hamamatsu Photonics K.K., ModelC4334).

Synthesis of Compounds (Synthesis Example 1) Synthesis of Compound 1

The compound (z) was synthesized according to the same method as in Adv.Opt. Mater. 4, 688-693 (2016).

Next, in a nitrogen stream atmosphere, 3,6-dimethylcarbazole (0.39 g,1.98 mmol) was added to a tetrahydrofuran solution (20 mL) of sodiumhydride (60% mineral oil dispersion, 0.08 g, 1.98 mmol), and stirred atroom temperature for 1 hour. The mixture was cooled to 0° C., and thecompound (z) (0.5 g, 0.79 mmol) was added thereto and stirred at 50° C.for 12 hours. The reaction mixture was quenched by adding it to waterwith ice, and then filtered to give a crude product. The resultant crudeproduct was purified through silica gel column chromatography(toluene/hexane=3:2) to give a yellow solid of the compound 1 (0.79 g,0.75 mmol, yield 95%).

¹H NMR: (500 MHz, acetone-d6): δ (ppm)=7.83 (d, J=8.2 Hz, 4H), 7.71 (d,J=7.1 Hz, 4H), 7.64 (d, J=8.3 Hz, 2H), 7.45 (d, J=8.4 Hz, 2H), 7.34 (d,J=7.2 Hz, 2H), 7.09 (m, 12H), 6.72 (t, J=7.9 Hz, 2H), 6.62 (d, J=8.4 Hz,2H), 6.45 (d, J=8.3 Hz, 4H), 2.11 (s, 12H)

(Synthesis Example 2) Synthesis of Compound 2

In a nitrogen stream atmosphere, 3,6-di-tert-butylcarbazole (1 g, 3.58mmol) was added to a tetrahydrofuran solution (20 mL) of sodium hydride(60% mineral oil dispersion, 0.14 g, 3.58 mmol), and stirred at roomtemperature for 1 hour. The mixture was cooled to 0° C., and thecompound (z) (1.04 g, 1.63 mmol) was added thereto and stirred at 50° C.for 12 hours. The reaction mixture was quenched by adding it to waterwith ice, and then filtered to give a crude product. The resultant crudeproduct was purified through silica gel column chromatography(toluene/hexane=1:1) to give a yellow solid of the compound 2 (1.8 g,1.56 mmol, yield 96%).

(Synthesis Example 3) Synthesis of Compound 3

In a nitrogen stream atmosphere, 3,6-diphenylcarbazole (1 g, 3.15 mmol)was added to a tetrahydrofuran solution (20 mL) of sodium hydride (60%mineral oil dispersion, 0.13 g, 3.15 mmol), and stirred at roomtemperature for 1 hour. The mixture was cooled to 0° C., and thecompound (z) (0.8 g, 1.26 mmol) was added thereto and stirred at 50° C.for 12 hours. The reaction mixture was quenched by adding it to waterwith ice, and then filtered to give a crude product. The resultant crudeproduct was purified through silica gel column chromatography(toluene/hexane=3:2) to give a yellow solid of the compound 3 (1.36 g,1.10 mmol, yield 87%).

¹H NMR: (500 MHz, acetone-d6): δ (ppm)=7.82 (m, 14H), 7.72 (d, J=8.7 Hz,4H), 7.45 (m, 8H), 7.35 (m, 10H), 7.26 (t, J=8.6 Hz, 4H), 7.16 (t, J=8.3Hz, 4H), 7.10 (t, J=7.9 Hz, 4H), 6.98 (d, J=8.6 Hz, 4H), 6.75 (m, 4H)

(Synthesis Example 4) Synthesis of Compound 4

The compound (y) was synthesized according to the same method as in Adv.Opt. Mater. 4, 688-693 (2016).

Next, in a nitrogen stream atmosphere, 3,6-dimethylcarbazole (0.37 g,1.92 mmol) was added to a tetrahydrofuran solution (20 mL) of sodiumhydride (60% mineral oil dispersion, 0.08 g, 1.92 mmol), and stirred atroom temperature for 1 hour. The mixture was cooled to 0° C., and thecompound (y) (1.0 g, 1.28 mmol) was added thereto and stirred at 50° C.for 12 hours. The reaction mixture was quenched by adding it to waterwith ice, and then filtered to give a crude product. The resultant crudeproduct was purified through silica gel column chromatography(toluene/hexane=3:2) to give a yellow solid of the compound 4 (1.08 g,1.13 mmol, yield 88%).

(Synthesis Example 5) Synthesis of Compound 5

In a nitrogen stream atmosphere, 3,6-di-tert-butylcarbazole (0.54 g,1.92 mmol) was added to a tetrahydrofuran solution (20 mL) of sodiumhydride (60% mineral oil dispersion, 0.08 g, 1.92 mmol), and stirred atroom temperature for 1 hour. The mixture was cooled to 0° C., and thecompound (y) (1.0 g, 1.28 mmol) was added thereto and stirred at 50° C.for 12 hours. The reaction mixture was quenched by adding it to waterwith ice, and then filtered to give a crude product. The resultant crudeproduct was purified through silica gel column chromatography(toluene/hexane=3:2) to give a yellow solid of the compound 5 (1.16 g,1.11 mmol, yield 87%).

(Synthesis Example 6) Synthesis of Compound 6

In a nitrogen stream atmosphere, 3,6-diphenylcarbazole (0.61 g, 1.92mmol) was added to a tetrahydrofuran solution (20 mL) of sodium hydride(60% mineral oil dispersion, 0.08 g, 1.92 mmol), and stirred at roomtemperature for 1 hour. The mixture was cooled to 0° C., and thecompound (y) (1.0 g, 1.28 mmol) was added thereto and stirred at 50° C.for 12 hours. The reaction mixture was quenched by adding it to waterwith ice, and then filtered to give a crude product. The resultant crudeproduct was purified through silica gel column chromatography(toluene/hexane=3:2) to give a yellow solid of the compound 6 (1.18 g,1.09 mmol, yield 85%).

¹H NMR: (500 MHz, acetone-d6): δ (ppm)=7.82 (m, 8H), 7.75 (m, 4H), 7.67(t, J=7.8 Hz, 4H), 7.45 (m, 4H), 7.35 (m, 8H), 7.25 (t, J=8.0 Hz, 2H),7.11 (m, 8H), 6.95 (d, J=8.6 Hz, 2H), 6.74 (m, 4H), 6.66 (t, J=7.8 Hz,4H)

(Synthesis Example 7) Synthesis of Compound 7

In a nitrogen stream atmosphere, 3,9′-bicarbazole (0.66 g, 1.98 mmol)was added to a tetrahydrofuran solution (15 mL) of sodium hydride (60%mineral oil dispersion, 0.08 g, 1.98 mmol), and stirred at roomtemperature for 1 hour. The mixture was cooled to 0° C., and thecompound (z) (0.5 g, 0.79 mmol) was added thereto and stirred at 50° C.for 12 hours. The reaction mixture was quenched by adding it to waterwith ice, and then filtered to give a crude product. The resultant crudeproduct was purified through silica gel column chromatography(toluene/hexane=1:1) to give a yellow solid of the compound 7 (0.54 g,0.43 mmol, yield 54%).

(Synthesis Example 8) Synthesis of Compound 11

In a nitrogen stream atmosphere, 3-methyl-9H-carbazole (0.51 g, 0.83mmol) was added to a tetrahydrofuran solution (15 mL) of sodium hydride(60% mineral oil dispersion, 0.15 g, 3.78 mmol), and stirred at roomtemperature for 1 hour. The mixture was cooled to 50° C., and thecompound (z) (0.6 g, 0.95 mmol) was added thereto and stirred at 50° C.for 12 hours. Water was added to the reaction mixture for precipitation,and the resultant precipitate was taken out through filtration. Thefiltered mixture was purified through silica gel column chromatography(toluene) to give the compound 11 (0.65 g, 0.68 mmol, yield 71.9%).

¹H-NMR (500 MHz, CDCl₃, δ):7.76-7.72 (m, 4H), 7.30-7.12 (m, 10H),7.10-7.02 (m, 10H), 6.98 (t, J=8.5 Hz, 2H), 6.91 (t, J=8.5 Hz, 2H),6.76-6.71 (m, 4H), 6.61-6.53 (m, 4H), 6.41 (t, J=8.5 Hz, 2H), 2.17-2.16(m, 6H)

ASAP Mass Spectrometry: Theoretical 956.4, Found 957.3.

(Synthesis Example 9) Synthesis of Compound 35

In a nitrogen stream atmosphere, tri(o-tolyl) phosphine (0.525 g, 1.72mmol) and tris(dibenzylideneacetone)palladium(0) (1.57 g, 1.72 mmol)were added to a toluene solution (50 mL) of tributyltin chloride (5.06g, 4.45 ml, 13.78 mmol) and 4-bromo-2,3,5,6-tetrafluorobenzonitrile(2.92 g, 11.50 mmol), heated up to 100° C., and stirred for 21 hours.The mixture was restored to room temperature, then quenched by addingwater thereto, extracted with ethyl acetate, and filtered throughCelite. Next, the organic layer was washed with saturated saline water,and dried with anhydrous magnesium sulfate. This was concentrated underreduced pressure, and the resultant mixture was purified through silicagel column chromatography (dichloromethane/hexane=1:2) to give a whitesolid of the compound (a) (2.42 g, 9.63 mmol, yield 83.7%).

¹H NMR (500 MHz, CDCl₃, δ): 7.56-7.51 (m, 3H), 7.48-7.45 (m, 2H)

ASAP Mass Spectrometry: Theoretical 251.0, Found 251.1.

In a nitrogen stream atmosphere, 9H-carbazole (0.397 g, 2.38 mmol) wasadded to a tetrahydrofuran solution (10 mL) of sodium hydride (60%mineral oil dispersion, 0.125 g, 3.14 mmol), and stirred at roomtemperature for 1 hour. The mixture was cooled to −50° C., and thecompound (a) (0.3 g, 1.19 mmol) was added thereto, then the cooling bathwas removed, and with gradually restoring to room temperature, this wasstirred for 22 hours. The reaction mixture was quenched by adding it towater with ice, then extracted with ethyl acetate, and the organic layerwas washed with saturated saline water, and dried with anhydrousmagnesium sulfate. This was concentrated under reduced pressure, and theresultant mixture was purified through silica gel column chromatography(chloroform/hexane=1:2) to give a yellow solid of the compound (b)(0.486 g, 0.89 mmol, yield 74.8%).

¹H NMR (500 MHz, CDCl₃, δ): 8.16 (d, J=7.5 Hz, 4H), 7.62-7.59 (m, 2H),7.54-7.49 (m, 7H), 7.38 (dt, J=7.5 Hz, 1.0 Hz, 4H), 7.30 (d, J=7.5 Hz,4H)

ASAP Mass Spectrometry: Theoretical 545.2, Found 545.2.

3-Phenyl-9H-carbazole (0.575 g, 2.36 mmol), potassium carbonate (0.702g, 3.94 mmol) and the compound (b) (0.5 g, 0.788 mmol) were put into a100-mL three-neck flask, which was then purged with nitrogen. Dewateredl-methyl-2-pyrrolidone (10 mL) was added to the mixture, and thenstirred in a nitrogen atmosphere under heat at 100° C. for 12 hours.After the stirring, the mixture was restored to room temperature, andthen water was added and filtered under suction. The resultant solid wasdissolved in toluene and purified through silica gel columnchromatography. The resultant fraction was concentrated andrecrystallized with a mixed solvent of chloroform and acetonitrile togive a pale yellow solid of the compound 35 (yield; 0.60 g, 77%).

¹H NMR (500 MHz, CDCl₃, δ): 7.77 (d, J=1.2, 2H), 7.55-7.69 (m, 4H), 7.60(d, J=7.5 Hz, 2H), 7.51 (dd, J=8.5 Hz, 4H), 7.42 (td, J=8.0, J=2.0, 4H),7.32-6.94 (m, 24H), 6.75 (d, J=7.5, 2H), 6.55 (td, J=7.51, J=1.2, 1H),6.46 (t, J=7.5, 2H)

ASAP Mass Spectrometry: Theoretical 991.37, Found 992.39.

(Synthesis Example 10) Synthesis of Compound 38

In a nitrogen stream atmosphere, the compound (b) (0.45 g, 0.825 mmol)prepared in Synthesis Example 9 was added to a 1-methyl-2-pyrrolidonesolution (10 mL) of 3,6-diphenylcarbazole (0.66 g, 2.06 mmol) andpotassium carbonate (0.43 g, 3.11 mmol), and stirred at 100° C. for 48hours. The mixture was restored to room temperature, then quenched byadding water thereto, extracted with ethyl acetate, and the organiclayer was washed with saturated saline water, and dried with anhydrousmagnesium sulfate. This was concentrated under reduced pressure, and theresultant mixture was purified through silica gel column chromatography(chloroform/hexane=1:1) to give a yellow solid of the compound 38 (0.575g, 0.502 mmol, yield 60.9%).

¹H NMR (500 MHz, CDCl₃, δ): 7.81 (d, J=1.5 Hz, 4H), 7.72-7.70 (m, 4H),7.54-7.52 (m, 8H), 7.43 (t, J=7.5 Hz, 8H), 7.32 (t, J=7.5 Hz, 4H),7.29-7.06 (m, 20H), 6.86-6.83 (m, 2H), 6.61-6.58 (m, 1H), 6.56-6.52 (m,2H)

ASAP Mass Spectrometry: Theoretical 1143.4, Found 1143.4.

(Synthesis Example 11) Synthesis of Compound 48

In a nitrogen stream atmosphere, 3,6-diphenylcarbazole (0.95 g, 2.97mmol) was added to a tetrahydrofuran solution (10 mL) of sodium hydride(60% mineral oil dispersion, 0.315 g, 7.88 mmol), and stirred at roomtemperature for 1 hour. The mixture was cooled to −50° C., and thecompound (a) (0.3 g, 1.19 mmol) prepared in Synthesis Example 9 wasadded thereto, then the cooling bath was removed, and with graduallyrestoring to room temperature, this was stirred for 17 hours. Thereaction mixture was quenched by adding it to water with ice, thenextracted with ethyl acetate, and the organic layer was washed withsaturated saline water, and dried with anhydrous magnesium sulfate. Thiswas concentrated under reduced pressure, and the resultant mixture waspurified through silica gel column chromatography(chloroform/hexane=1:2) to give a yellow solid of the compound (c)(0.308 g, 0.362 mmol, yield 30.4%), and a yellow solid of the compound(d) (0.70 g, 0.609 mmol, yield 51.2%).

Compound (c):

¹H NMR (500 MHz, CDCl₃, δ): 8.42 (d, J=1.0 Hz, 4H), 7.80 (dd, J=7.0 Hz,2.0 Hz, 4H), 7.74 (dd, J=8.0 Hz, 1.0 Hz, 8H), 7.68-7.65 (m, 2H),7.58-7.48 (m, 11H), 7.42 (d, J=8.0 Hz, 4H), 7.40-7.36 (m, 4H)

ASAP Mass Spectrometry: Theoretical 849.3, Found 849.3.

Compound (d):

¹H NMR (500 MHz, CDCl₃, δ): 8.47 (d, J=1.5 Hz, 2H), 7.89 (dd, J=8.5 Hz,2.0 Hz, 2H), 7.83 (d, J=1.5 Hz, 2H), 7.80-7.78 (m, 4H), 7.74 (d, J=1.5Hz, 2H), 7.66 (d, J=8.0 Hz, 2H), 7.54-7.52 (m, 4H), 7.48-7.44 (m, 8H),7.42-7.27 (m, 18H), 7.19-7.16 (m, 7H), 7.01 (d, J=8.0 Hz, 2H)

ASAP Mass Spectrometry: Theoretical 1148.4, Found 1148.4.

In a nitrogen stream atmosphere, the compound (c) (0.30 g, 0.35 mmol)was added to a 1-methyl-2-pyrrolidone solution (10 mL) of 9H-carbazole(0.175 g, 1.05 mmol) and potassium carbonate (0.184 g, 1.33 mmol), andstirred at 100° C. for 20 hours. The mixture was restored to roomtemperature, then quenched by adding water thereto, extracted with ethylacetate, and the organic layer was washed with saturated saline water,and dried with anhydrous magnesium sulfate. This was concentrated underreduced pressure, and the resultant mixture was purified through silicagel column chromatography (chloroform/hexane=1:2) to give a yellow solidof the compound 48 (0.317 g, 0.277 mmol, yield 79.1%).

¹H NMR (500 MHz, CDCl₃, δ): 7.96 (d, J=1.5 Hz, 4H), 7.59-7.55 (m, 12H),7.45 (t, J=7.5 Hz, 8H), 7.35-7.31 (m, 12H), 7.07-7.01 (m, 4H), 7.00-6.94(m, 8H), 6.76-6.74 (m, 2H), 6.58-6.54 (m, 1H), 6.45 (t, J=8.0 Hz, 2H)

ASAP Mass Spectrometry: Theoretical 1143.4, Found 1143.3.

(Synthesis Example 12) Synthesis of Compound 55

In a nitrogen stream atmosphere, 9H-carbazole (4.78 g, 28.59 mmol) wasadded to a tetrahydrofuran solution (120 mL) of sodium hydride (60%mineral oil dispersion, 0.90 g, 22.51 mmol), and stirred for 1 hour. Themixture was cooled to −50° C., and 2,3,5,6-tetrafluorobenzonitrile (2.50g, 14.28 mmol) was added thereto, then the cooling bath was removed, andwith gradually restoring to room temperature, this was stirred for 110hours. The reaction mixture was quenched by adding it to water with ice,then extracted with ethyl acetate, and the organic layer was washed withsaturated saline water, and dried with anhydrous magnesium sulfate. Thiswas concentrated under reduced pressure, and the resultant mixture waspurified through silica gel column chromatography (toluene/hexane=1:1)to give a pale yellow solid of the compound (e) (2.42 g, 5.15 mmol,yield 36.1%).

¹H NMR (500 MHz, CDCl₃, δ): 8.16 (d, J=7.5 Hz, 4H), 7.68 (t, J_(H-F)=9.0HZ, 1H), 7.51 (dt, J=7.5 Hz, 1.0 Hz, 4H), 7.38 (dt, J=7.5 Hz, 1.0 Hz,4H), 7.23 (d, J=7.5 Hz, 4H)

ASAP Mass Spectrometry: Theoretical 469.1, Found 469.1.

In a nitrogen stream atmosphere, the compound (e) (0.34 g, 0.724 mmol)was added to a 1-methyl-2-pyrrolidone solution (9 mL) of3,6-diphenylcarbazole (0.57 g, 1.81 mmol) and potassium carbonate (0.38g, 2.75 mmol), and stirred at 100° C. for 24 hours. The mixture wasrestored to room temperature, then quenched by adding water thereto,extracted with ethyl acetate, and the organic layer was washed withsaturated saline water, and dried with anhydrous magnesium sulfate. Thiswas concentrated under reduced pressure, and the resultant mixture waspurified through silica gel column chromatography (toluene/hexane=1:1)to give a yellow solid of the compound 55 (0.515 g, 0.482 mmol, yield66.6%).

¹H NMR (500 MHz, CDCl₃, δ): 8.54 (s, 1H), 8.04 (s, 4H), 7.81 (d, J=7.5Hz, 4H), 7.61-7.59 (m, 8H), 7.47-7.39 (m, 20H), 7.36-7.33 (m, 4H),7.25-7.22 (m, 4H), 7.18-7.15 (m, 4H)

ASAP Mass Spectrometry: Theoretical 1067.4, Found 1067.4.

(Synthesis Example 13) Synthesis of Compound 108

3.6-Dimethyl-9H-carbazole (1.56 g, 9.00 mmol) and sodium hydride (0.400g, 60% mineral oil dispersion, 1.00 mmol) were put into a 100-mLthree-neck flask, which was then purged with nitrogen. Dewateredtetrahydrofuran (80 mL) was added to the mixture, then stirred in anitrogen atmosphere for 1 hour, and tetrafluoroterephthalonitrile (0.8g, 4.00 mmol) was added thereto. The mixture was stirred under heat at50° C. for 12 hours, then restored to room temperature, and water wasadded and filtered under suction to give a solid. The resultant solidwas purified through sublimation to give a red solid of the compound (f)(yield: 0.8 g, 36%).

3.6-Diphenyl-9H-carbazole (0.696 g, 2.18 mmol), potassium carbonate(0.647 g, 3.63 mmol) and the compound (f) (0.4 g, 0.726 mmol) were putinto a 100-mL three-neck flask, which was then purged with nitrogen.Dewatered 1-methyl-2-pyrrolidone (10 mL) was added to the mixture, thenstirred in a nitrogen atmosphere under heat at 100° C. for 12 hour.After the stirring, the mixture was restored to room temperature, andwater was added thereto and filtered under suction. The resultant solidwas recrystallized with a mixed solvent of chloroform and acetonitrileto give a red solid of the compound 108 (yield: 0.62 g, 74%).

¹H NMR (500 MHz, CDCl₃, δ): 8.01 (d, J=1.5 Hz, 4H), 7.62 (dd, J=8.0 Hz,J=1.0 Hz, 8H), 7.50-7.43 (m, 12H), 7.41 (dd, J=7.5, J=1.5, 4H), 7.37 (t,J=7.5, 4H), 7.33 (d, J=8.5 Hz, 4H), 7.17 (d, J=8 Hz, 4H), 6.99 (dd, J=8Hz, J=1.5 Hz, 4H), 2.41 (s, 12H)

ASAP Mass Spectrometry: Theoretical 1148.46, Found 1150.51.

(Synthesis Example 14) Synthesis of Compound 149

In a nitrogen stream atmosphere, the compound (d) (0.65 g, 0.566 mmol)was added to a 1-methyl-2-pyrrolidone solution (10 mL) of 9H-carbazole(0.142 g, 0.849 mmol) and potassium carbonate (0.18 g, 1.30 mmol), andstirred at 100° C. for 120 hours. The mixture was restored to roomtemperature, and quenched by adding water thereto. The resultantprecipitate was washed with methanol, and this was purified throughsilica gel column chromatography (toluene/hexane=3:2) to give an orangesolid of the compound 149 (0.284 g, 0.219 mmol, yield 38.7%).

¹H NMR (500 MHz, CDCl₃, δ): 7.98 (d, J=1.0 Hz, 2H), 7.85 (d, J=1.0 Hz,2H), 7.73 (d, J=2.0 Hz, 2H), 7.60-7.58 (m, 6H), 7.49-7.44 (m, 12H),7.39-7.24 (m, 20H), 7.19-7.16 (m, 4H), 7.12-7.09 (m, 2H), 7.05-6.97 (m,6H), 6.93 (d, J=8.0 Hz, 2H), 6.64 (t, J=8.0 Hz, 1H), 6.58 (t, J=8.0 Hz,2H)

ASAP Mass Spectrometry: Theoretical 1295.5, Found 1295.2.

(Synthesis Example 15) Synthesis of Compound 150

In a nitrogen stream atmosphere, the compound (e) (0.50 g, 1.07 mmol)was added to a 1-methyl-2-pyrrolidone solution (10 mL) of3-methyl-9H-carbazole (0.57 g, 3.20 mmol) and potassium carbonate (0.95g, 5.33 mmol), and stirred at 120° C. for 36 hours. The mixture wasrestored to room temperature, then precipitated by adding water thereto,and the precipitate was taken out through filtration. The filteredmixture was purified through silica gel column chromatography (toluene)to give the compound 150 (0.40 g, 0.51 mmol, yield 47.4%).

¹H NMR (500 MHz, CDCl₃, δ): 8.38 (s, 1H), 7.83-7.79 (m, 4H), 7.75-7.72(m, 2H), 7.58 (d, J=4.0 Hz, 2H), 7.43-7.33 (m, 4H), 7.30-7.11 (m, 12H),7.10-7.03 (m, 4H), 7.00-6.93 (m, 2H), 2.41 (s, 3H), 2.39 (s, 3H)

ASAP Mass Spectrometry: Theoretical 791.3, Found 792.4

(Synthesis Example 16) Synthesis of Compound 151

In an argon stream atmosphere, 4-bromo-2,3,5,6-tetrafluorobenzonitrile(3 g, 11.9 mmol) was dissolved in toluene (100 mL), and an aqueous 0.3 Msodium carbonate solution (67 mL) was added thereto. Pd(PPh₃)₄ (1.38 g,1.19 mmol) and 5′-m-tetraphenylboronic acid (3.92 g, 14.3 mmol) wereadded, and heated overnight under reflux. This was cooled to roomtemperature, then the organic layer was separated, and the aqueous layerwas extracted with dichloromethane. The organic layers were combined,and dried with anhydrous sodium sulfate. The desiccant was filtered out,and the filtrate was concentrated by distillation under reduced pressureto give a crude product. The resultant crude product was purifiedthrough silica gel column chromatography (hexane/chloroform=4:1) to givea white powder of the compound (i) (2.37 g, 5.88 mmol, yield 49.4%).

In an argon stream atmosphere, 9H-carbazole (0.83 g, 4.96 mmol) wasadded to a tetrahydrofuran solution (50 mL) of sodium hydride (60%mineral oil dispersion, 0.2 g, 4.96 mmol), and stirred at roomtemperature for 1 hour. The mixture was cooled to −50° C., and thecompound (i) (1.0 g, 2.48 mmol) was added thereto, then the cooling bathwas removed, and with gradually restoring to room temperature, this wasstirred for 2 hours. The reaction mixture was quenched by adding it towater with ice, then extracted with dichioromethane, and the organiclayer was washed with saturated saline water, and dried with anhydrousmagnesium sulfate. This was concentrated under reduced pressure, and theresultant mixture was purified through silica gel column chromatography(hexane/toluene=3:2) to give a white solid of the compound (j) (0.96 g,1.38 mmol, yield 55.6%).

In an argon stream atmosphere, 3,6-diphenylcarbazole (1.32 g, 4.14 mmol)was added to a tetrahydrofuran solution (30 mL) of sodium hydride (60%mineral oil dispersion, 0.17 g, 4.14 mmol), and stirred at roomtemperature for 1 hour. The compound (j) (0.96 g, 1.38 mmol) was addedthereto, and heated overnight at 50° C. The reaction mixture wasquenched by adding it to water with ice to collect a solid. Theresultant solid was purified through silica gel column chromatography(toluene) to give a yellow solid of the compound 151 (1.10 g, 0.85 mmol,yield 61.5%).

(Synthesis Example 17) Synthesis of Compound 152

In a nitrogen stream atmosphere, 9H-carbazole (0.80 g, 4.78 mmol) wasadded to a tetrahydrofuran solution (15 mL) of sodium hydride (60%mineral oil dispersion, 0.17 g, 7.17 mmol), and stirred at roomtemperature for 1 hour. The mixture was cooled to −50° C., and thecompound 1 (0.4 g, 1.59 mmol) was added thereto, then the cooling bathwas removed, and with gradually restoring to room temperature, this wasstirred for 24 hours. The reaction mixture was quenched by adding it towater with ice, then extracted with ethyl acetate, and the organic layerwas washed with saturated saline water, and dried with anhydrousmagnesium sulfate. This was concentrated under reduced pressure, and theresultant mixture was purified through silica gel column chromatography(hexane/toluene=2:1) to give a yellow solid of the compound (h) (0.69 g,1.00 mmol, yield 62.9%).

¹H NMR (500 MHz, CDCl₃, δ): 8.20 (d, J=8.5 Hz, 2H), 7.72-7.68 (m, 2H),7.61-7.56 (m, 4H), 7.51 (d, J=8.5 Hz, 2H), 7.44 (t, J=8.5 Hz, 2H),7.16-7.11 (m, 4H), 7.10-6.94 (m, 13H)

ASAP Mass Spectrometry: Theoretical 692.2, Found 692.1.

In a nitrogen stream atmosphere, the compound (h) (0.50 g, 0.72 mmol)was added to a 1-methyl-2-pyrrolidone solution (10 mL) of3,6-diphenylcarbazole (0.35 g, 1.08 mmol) and potassium carbonate (0.20g, 1.44 mmol), and stirred at room temperature for 48 hours. The mixturewas restored to room temperature, quenched by adding water thereto, andthe resultant precipitate was washed with methanol. This wasreprecipitated in chloroform/methanol to give a yellow solid of thecompound 152 (0.56 g, 0.564 mmol, yield 77.6%).

¹H NMR (500 MHz, CDCl₃, δ): 7.80 (d, J=1.5 Hz, 2H), 7.73-7.68 (m, 4H),7.59-7.57 (m, 2H), 7.52 (dd, J=8.0 Hz, J=1.5 Hz, 4H), 7.42 (t, J=8.0 Hz,4H), 7.33-7.22 (m, 6H), 7.19 (dd, J=8.0 Hz, J=1.5 Hz, 2H), 7.14-6.92 (m,16H), 6.74 (dd, J=8.0 Hz, J=1.5 Hz, 2H), 6.55 (t, J=8.0 Hz, 1H), 6.48(t, J=8.0 Hz, 2H)

ASAP Mass Spectrometry: Theoretical 991.4, Found 991.8.

(Synthesis Example 18) Synthesis of Compound 313

In a nitrogen stream atmosphere, 9H-carbazole (1.42 g, 8.49 mmol) wasadded to a tetrahydrofuran solution (45 mL) of sodium hydride (60%mineral oil dispersion, 0.265 g, 6.63 mmol), and stirred at roomtemperature for 1 hour. The mixture was cooled to −50° C., and2,3,5,6-tetrafluoro-4-pyridinecarbonitrile (0.749 g, 4.25 mmol) wasadded thereto, then the cooling bath was removed, and with graduallyrestoring to room temperature, this was stirred for 24 hours. Thereaction mixture was quenched by adding it to water with ice, thenextracted with ethyl acetate, and the organic layer was washed withsaturated saline water, and dried with anhydrous magnesium sulfate. Thiswas concentrated under reduced pressure, and the resultant mixture wasreprecipitated in ethyl acetate/methanol to give an orange solid of thecompound (g) (0.989 g, 2.10 mmol, yield 49.4%).

¹H NMR (500 MHz, CDCl₃, δ): 8.19 (d, J=7.5 Hz, 2H), 8.15 (d, J=7.5 Hz,2H), 7.69-7.67 (m, 2H), 7.54 (dt, J=7.5, 1.0 Hz, 4H), 7.44 (dt, J=7.5,1.5 Hz, 4H), 7.30 (d, J=8.0 Hz, 2H)

¹³C-NMR (125 MHz, CDCl₃, δ): 154.66, 154.64, 152.67, 152.65, 150.66,150.62, 148.47, 148.43, 139.63, 138.59, 126.80, 126.76, 125.14, 124.55,122.71, 122.14, 120.98, 120.54, 120.02, 119.75, 115.74, 115.69, 115.62,115.57, 111.53, 111.50, 109.74, 108.76, 108.73

ASAP Mass Spectrometry: Theoretical 470.1, Found 470.1.

In a nitrogen stream atmosphere, the compound (g) (0.50 g, 1.06 mmol)was added to a 1-methyl-2-pyrrolidone solution (13 mL) of3,6-diphenylcarbazole (0.849 g, 2.66 mmol) and potassium carbonate (0.55g, 3.99 mmol), and stirred at 100° C. for 48 hours. The mixture wasrestored to room temperature, quenched by adding water thereto,extracted with ethyl acetate, and the organic layer was washed withsaturated saline water, and dried with anhydrous magnesium sulfate. Thiswas concentrated under reduced pressure, and the resultant mixture waspurified through silica gel column chromatography (toluene/hexane=1:1)to give an orange solid of the compound 313 (0.963 g, 0.901 mmol, yield84.7%).

¹H NMR (500 MHz, CDCl₃ δ): 8.07 (d, J=1.5 Hz, 2H), 8.00 (d, J=1.5 Hz,2H), 7.84 (d, J=7.0 Hz, 2H), 7.76 (d, J=7.0 Hz, 2H), 7.63 (d, J=8.0 Hz,4H) 7.58 (d, J=8.0 Hz, 4H), 7.54-7.43 (m, 14H), 7.38-7.32 (m, 8H),7.30-7.07 (m, 10H)

ASAP Mass Spectrometry: Theoretical 1068.4, Found 1068.3.

Measurement of ΔE_(st)

The lowest excited singlet energy level E_(S1) and the lowest excitedtriplet energy level E_(T1) of the synthesized compounds were measuredaccording to the following process. In addition, the energy differenceΔE_(st) between the lowest excited singlet state and the lowest excitedtriplet state at 77K was determined by calculating the differencebetween E_(S1) and E_(T1).

(1) Lowest Excited Singlet Energy Level E_(S1)

The compound to be analyzed was vapor-deposited on an Si substrate toprepare a sample, and the fluorescent spectrum of the sample wasmeasured at room temperature (300 K). For the fluorescent spectrum, theemission intensity was on the vertical axis and the wavelength was onthe horizontal axis. A tangent line was drawn to the rising of theemission spectrum on the short wavelength side, and the wavelength valuekedge [nm] at the intersection between the tangent line and thehorizontal axis was read. The wavelength value was converted into anenergy value according to the following conversion expression tocalculate E_(S1).

E_(S1)[eV]=1239.85λedge  Conversion Expression:

For the measurement of the emission spectrum, a nitrogen laser(available from Lasertechnik Berlin, MNL200) was used as an excitationlight source along with a streak camera (available from HamamatsuPhotonics K.K., C4334) as a detector.

(2) Lowest Excited Triplet Energy Level E_(T1)

The same sample as that for measurement of the singlet energy levelE_(S1) was cooled to 77 [K], and the sample for phosphorescencemeasurement was irradiated with excitation light (337 nm), and using astreak camera, the phosphorescence intensity thereof was measured. Atangent line was drawn to the rising of the phosphorescent spectrum onthe short wavelength side, and the wavelength value λedge [nm] at theintersection between the tangent line and the horizontal axis was read.The wavelength value was converted into an energy value according to thefollowing conversion expression to calculate E_(T1).

E_(T1)[eV]=1239.85/λedge  Conversion Expression:

The tangent line to the rising of the phosphorescent spectrum on theshort wavelength side was drawn as follows. While moving on the spectralcurve from the short wavelength side of the phosphorescent spectrumtoward the maximum value on the shortest wavelength side among themaximum values of the spectrum, a tangent line at each point on thecurve toward the long wavelength side was taken into consideration. Withrising thereof (that is, with increase in the vertical axis), theinclination of the tangent line increases. The tangent line drawn at thepoint at which the inclination value has a maximum value was referred toas the tangent line to the rising on the short wavelength side of thephosphorescent spectrum.

The maximum point having a peak intensity of 10% or less of the maximumpeak intensity of the spectrum was not included in the maximum value onthe above-mentioned shortest wavelength side, and the tangent line drawnat the point which is closest to the maximum value on the shortestwavelength side and at which the inclination value has a maximum valuewas referred to as the tangent line to the rising on the shortwavelength side of the phosphorescent spectrum.

Found data of ΔE_(st) of each compound are shown in the following Table.

TABLE 10 Light-emitting ΔE_(st) material (eV) Compound 1  0.16 Compound2  0.17 Compound 3  0.16 Compound 4  0.15 Compound 6  0.16 Compound 11 0.11 Compound 35  0.12 Compound 38  0.13 Compound 55  0.17 Compound 1500.15 Compound 151 0.11 Compound 152 0.09

Production and Evaluation of Organic Electroluminescent Device Example 1

On a glass substrate having, as formed thereon, an anode of indium tinoxide (ITO) having a thickness of 110 nm, thin films were laminatedaccording to a vacuum evaporation method under a vacuum degree of5.0×10⁻⁵ Pa or less. First, on ITO, HATCN was formed to have a thicknessof 60 nm, then TrisPCz was formed thereon to have a thickness of 30 nm,and further thereon, mCBP was formed to have a thickness of 5 nm. Next,mCBP, the compound 1 and TBPb were co-deposited from differentevaporation sources to form a layer having a thickness of 30 nm to be alight-emitting layer. At that time, the concentration of the compound 1was 20% by weight, and the concentration of TBPb was 0.5% by weight.Next, SF3TRZ was formed to have a thickness of 10 nm, and SF3TRZ:Liq(weight ratio 7:3) was formed thereon to have a thickness of 30 nm.Further, Liq:Al (weight ratio 1:50) was vapor-deposited thereon to forma cathode, thereby producing an organic electroluminescent device,called device 1.

Other devices 2 to 8 were produced in the same manner as above, exceptthat, as shown in the following Table, the concentration of the secondorganic compound in the light-emitting layer was changed, a compound A(ΔE_(st)=0.17 eV) was used in place of the compound 1 in thelight-emitting layer, and DPEPO was used in place of mCBP in thelight-emitting layer.

These devices 1 to 8 all emitted delayed fluorescence, and the maximumemission wavelength and the external quantum efficiency at 0.01 mA/cm²thereof are as shown in the following Table. These all have a markedlyimproved external quantum efficiency as compared with a comparativedevice in which the second organic compound was not used in thelight-emitting layer and, in place of using the second organic compoundtherein, the amount of the first organic compound in the layer wasincreased. In particular, the devices 1, 3, 5 and 7 using, as the secondorganic compound, the compound 1 in which all the five carbazol-9-ylgroups bonding to benzonitrile were not the same had a further markedlyincreased external quantum efficiency as compared with the devices 2, 4,6 and 8 using the compound A in which all the five carbazol-9-yl groupsbonding to benzonitrile were the same.

TABLE 11 Composition of light-emitting layer External quantum Maximum (%by weight) efficiency, emission First organic Second organic Thirdorganic at 0.01 mA/cm² wavelength compound compound compound (%) (nm)Device 1 mCBP (79.5) Compound 1 (20) TBPe (0.5) 18.4 500 Device 2 mCBP(79.5) Compound A (20) TBPe (0.5) 14.5 496 Device 3 mCBP (89.5) Compound1 (10) TBPe (0.5) 18.5 496 Device 4 mCBP (89.5) Compound A (10) TBPe(0.5) 15.3 495 Device 5 DPEPO (79.5) Compound 1 (20) TBPe (0.5) 14.8 504Device 6 DPEPO (79.5) Compound A (20) TBPe (0.5) 12.7 495 Device 7 DPEPO(89.5) Compound 1 (10) TBPe (0.5) 12.2 500 Device 8 DPEPO (89.5)Compound A (10) TBPe (0.5) 11.7 493

Example 2

On a glass substrate having, as formed thereon, an anode of indium tinoxide (ITO) having a thickness of 110 nm, thin films were laminatedaccording to a vacuum evaporation method under a vacuum degree of5.0×10⁻⁵ Pa or less. First, on ITO, HATCN was formed to have a thicknessof 10 nm, then TrisPCz was formed thereon to have a thickness of 5 nm,and further thereon, mCBP was formed to have a thickness of 5 nm. Next,mCBP, the compound 3 and TTPA were co-deposited from differentevaporation sources to form a layer having a thickness of 30 nm to be alight-emitting layer. At that time, the concentration of the compound 3was 20% by weight, and the concentration of TTPA was 0.5% by weight.Next, SF3TRZ was formed to have a thickness of 10 nm, and SF3TRZ:Liq(weight ratio 7:3) was formed thereon to have a thickness of 40 nm.Further, Liq:Al (weight ratio 1:50) was vapor-deposited thereon to forma cathode, thereby producing an organic electroluminescent device,called device 9.

Other devices 10 to 12 were produced in the same manner as above, exceptthat, as shown in the following Table, the compound A was used in placeof the compound 3 in the light-emitting layer, and 2DPhAPA was used inplace of TTPA in the light-emitting layer.

These devices 9 to 12 all emitted delayed fluorescence, and the maximumemission wavelength and the external quantum efficiency at 0.01 mA/cm²and 1000 cd/m² thereof are as shown in the following Table. These allhave a markedly improved external quantum efficiency and a longerlifetime as compared with a comparative device in which the secondorganic compound was not used in the light-emitting layer and, in placeof using the second organic compound therein, the amount of the firstorganic compound in the layer was increased. In particular, the device 9using, as the second organic compound, the compound 3 in which all thefive carbazol-9-yl groups bonding to benzonitrile were not the same hada further markedly increased external quantum efficiency and a longerlifetime as compared with the device 10 using the compound A in whichall the five carbazol-9-yl groups bonding to benzonitrile were the same.The same tendency was recognized also in the device 12 using thecompound A and the device 11 using the compound 3.

TABLE 12 Maximum Composition of light-emitting layer (% by weight)Emission First organic Second organic Third organic External quantumefficiency (%) LT95 (hr) Wavelength compound compound compound at 0.01mA/cm² at 1000 cd/m² at 1000 cd/m² (nm) Device 9 mCBP (79.5) Compound 3(20) TTPA (0.5) 16.0 13.9 214 532 Device 10 mCBP (79.5) Compound A (20)TTPA (0.5) 14.3 12.3 36 531 Device 11 mCBP (89.5) Compound 3 (20)2DPhAPA (0.5) 14.2 12.3 84 512 Device 12 mCBP (89.5) Compound A (20)2DPhAPA (0.5) 13.8 10.6 13 508

Organic electroluminescent devices produced using any of the compounds2, 4 to 7, 11, 35, 38, 48, 55, 108, 149, 150, 151, 152, 313, thecompound b, and the compound d in place of the compound 1 in the device1 also have excellent external quantum efficiency and lifetimecomparable to those of the device 1.

Example 3

Organic electroluminescent devices produced in the same manner as in thedevice 1, except that the combination of the second organic compound andthe third organic compound in the light-emitting layer in the device 1was changed to a combination of the second organic compound and thethird organic compound of the combinations 1 to 16950 shown in Table 9,are referred to as devices 1a to 16950a.

Organic electroluminescent devices produced in the same manner as in thedevice 9, except that the combination of the second organic compound andthe third organic compound in the light-emitting layer in the device 9was changed to a combination of the second organic compound and thethird organic compound of the combinations 1 to 16950 shown in Table 9,are referred to as devices 1b to 16950b.

Example 4

The device 1 has a markedly improved external quantum efficiency and alonger lifetime as compared with devices 1B to 1K produced using thefollowing compounds B to K in place of the compound 1 in the device 1.

The device 9 has a markedly improved heat resistance and a longerlifetime as compared with devices 9B to 9K produced using the followingcompounds B to K in place of the compound 3 in the device 9.

INDUSTRIAL APPLICABILITY

The organic electroluminescent device of the present invention has ahigh light emission efficiency, and is therefore applicable to variousinstruments as image display devices. Consequently, the industrialapplicability of the present invention is great.

REFERENCE SIGNS LIST

-   1 Substrate-   2 Anode-   3 Hole Injection Layer-   4 Hole Transport Layer-   5 Light-Emitting Layer-   6 Electron Transport Layer-   7 Cathode

1. An organic electroluminescent device having an anode, a cathode, andat least one organic layer that contains a light-emitting layer betweenthe anode and the cathode, wherein: the light-emitting layer contains atleast a first organic compound, a second organic compound and a thirdorganic compound satisfying the following formula (A), the secondorganic compound is a delayed fluorescent material, and the thirdorganic compound is a light-emitting material:E_(S1)(A)>E_(S1)(B)>E_(S1)(C)  Formula (A) wherein E_(S1)(A) representsa lowest excited singlet energy level of the first organic compound,E_(S1)(B) represents a lowest excited singlet energy level of the secondorganic compound, E_(S1)(C) represents a lowest excited singlet energylevel of the third organic compound.
 2. The organic electroluminescentdevice according to claim 1, wherein the second organic compound is suchthat the energy difference ΔE_(st) between the lowest excited singletstate and the lowest excited triplet state at 77 K thereof is 0.3 eV orless.
 3. The organic electroluminescent device according to claim 1,wherein the second organic compound is such that the energy differenceΔE_(st) between the lowest excited singlet state and the lowest excitedtriplet state at 77 K thereof is 0.08 eV or less.
 4. The organicelectroluminescent device according to claim 1, wherein the firstorganic compound and the second organic compound satisfy the followingformula (B):E_(T1)(A)>E_(T1)(B)  Formula (B) wherein E_(T1)(A) represents a lowestexcited triplet energy level at 77 K of the first organic compound,E_(T1)(B) represents a lowest excited triplet energy level at 77 K ofthe second organic compound.
 5. The organic electroluminescent deviceaccording to claim 1, wherein the third organic compound emitsfluorescence when returning back to the ground state energy level fromthe lowest excited singlet energy level.
 6. The organicelectroluminescent device according to claim 1, wherein the content ofthe second organic compound in the light-emitting layer is smaller thanthe content of the first organic compound therein.
 7. The organicelectroluminescent device according to claim 1, wherein thelight-emitting layer contains two or more compounds as the third organiccompound.
 8. The organic electroluminescent device according to claim 1,wherein the light-emitting layer contains one or more organic compoundsin addition to the first organic compound, the second organic compoundand the third organic compound.
 9. The organic electroluminescent deviceaccording to claim 1, wherein the second organic compound is a compoundrepresented by the following general formula (1):(A)m-L-(D)n  General Formula (1) wherein L represents an (m+n)-valentaromatic linking group; A represents a group having a positive Hammett'sσ_(P) value, or a phenyl group; D represents a group having a negativeHammett's σ_(p) value (except a phenyl group); m represents an integerof 1 or more; n represents an integer of 2 or more; when m is 2 or more,plural A's may be the same as or different from each other; two ofplural D's are groups containing an aromatic ring common to them buthaving a different structure.
 10. The organic electroluminescent deviceaccording to claim 1, wherein the second organic compound is a compoundrepresented by the following general formula (12):

wherein at least three of R¹¹ to R¹⁵ are selected from a substituted orunsubstituted diarylamino group (provided that the two aryl groupsconstituting the diarylamino group may bond to each other) and a halogenatom, and all the selected groups are not the same, and at least one isa substituted or unsubstituted diarylamino group (provided that the twoaryl groups constituting the diarylamino group may bond to each other),and the remaining 0 to 2 each represent a hydrogen atom, a substitutedor unsubstituted aryl group, or a cyano group.
 11. The organicelectroluminescent device according to claim 1, wherein the secondorganic compound is a compound represented by the following generalformula (14):

wherein at least three of R¹¹, R¹², R¹⁴ and R¹⁵ are selected from asubstituted or unsubstituted diarylamino group (provided that the twoaryl groups constituting the diarylamino group may bond to each other)and a halogen atom, and all the selected groups are not the same, and atleast one is a substituted or unsubstituted diarylamino group(providedthat the two aryl groups constituting the diarylamino group may bond toeach other), and the remaining 0 to 1 represents a hydrogen atom, asubstituted or unsubstituted aryl group, or a cyano group.
 12. Acompound represented by the following general formula (13):

wherein at least three of R¹¹ to R¹⁵ each represent a substituted orunsubstituted carbazol-9-yl group, and all these at least threesubstituted or unsubstituted carbazol-9-yl groups are not the same, andare not substituted with a substituted or unsubstituted diarylaminogroup (provided that the two aryl groups constituting the diarylaminogroup may bond to each other), the remaining 0 to 2 each represent ahydrogen atom, a substituted or unsubstituted aryl group, a halogenatom, or a cyano group.
 13. The organic electroluminescent deviceaccording to claim 9, wherein A is a cyano group.
 14. The organicelectroluminescent device according to claim 9, wherein D is adiarylamino group or a carbazolyl group.
 15. The organicelectroluminescent device according to claim 9, wherein the secondorganic compound is a compound represented by the following generalformula (10):

wherein A¹ represents a group having a positive Hammett's σ_(p) value,R¹ to R⁵ each represent a hydrogen atom, a group having a positiveHammett's σ_(p) value, or a group having a negative Hammett's σ_(p)value, and at least two of R¹ to R⁵ each are a group having a negativeHammett's σ_(p) value (except a phenyl group); when one or more of R¹ toR⁵ each are a group having a positive Hammett's σ_(p) value, the grouphaving a positive Hammett's σ_(p) value represented by A¹ and the grouphaving a positive Hammett's σ_(p) value of R¹ to R⁵ may be the same asor different from each other.
 16. The organic electroluminescent deviceaccording to claim 15, wherein A¹ is a cyano group, and at least four ofR¹ to R⁵ each are a group having a negative Hammett's σ_(p) value(except a phenyl group).
 17. The organic electroluminescent deviceaccording to claim 16, wherein R¹ and R⁵ each are a group having anegative Hammett's σ_(p) value (except a phenyl group).
 18. The organicelectroluminescent device according to claim 15, wherein R¹ and R⁵ havesame structure and are a group having a negative Hammett's σ_(p) value(except a phenyl group).
 19. The organic electroluminescent deviceaccording to claim 15, wherein R¹ and R⁴ have same structure and are agroup having a negative Hammett's σ_(P) value (except a phenyl group).20. The organic electroluminescent device according to claim 15, whereinR¹ and two of R² to R⁵ each are a group having a negative Hammett'sσ_(p) value (except a phenyl group).
 21. The organic electroluminescentdevice according to claim 15, wherein R¹, R⁵ and two of R² to R⁴ eachare a group having a negative Hammett's σ_(p) value (except a phenylgroup).
 22. The organic electroluminescent device according to claim 15,wherein at least four of R¹ to R⁵ each are a group having a negativeHammett's σ_(p) value (except a phenyl group), two of the at least fourof R¹ to R⁵ have a first common structure and the others have a commonsecond structure that differs from the first common structure.